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There is no *need* to upgrade Windows (or hardware) if the "old" system/OS does the tasks required.  As I've frequently stated, I'm using a 14-years-old NT4 system at work that has been running 24/7 for the duration, other than the occasional reboot, shutdown for extended power failures or maintenance such as blowing out accumulated dust.  It's used for an ancient DOS accounting package (Solomon III, which BTW is Y2K-compliant), faxing, minor bit of word processing, and keeping the business's web site updated.  Win7 wouldn't do those tasks any better.  That being said, I'm prepping to change the hardware just on the point of concern on age (although it'd be much more interesting to see how much longer the system will keep going).  Problem is the voicemail/fax software won't work on anything newer than Win98 or NT (does not work on 2K).  A stand-alone fax solves the fax issue, but not voicemail ... which voicemail really isn't so much needed any longer anyway.  The accounting software works on XP, but I don't know about Win7 without testing.  The Win7 system I have (see below) is 64-bit and Solomon does not run on 64-bit.  So ... I'd like to go with XP if I can get it to install and activate.

I switched to XP from Win2K on my main personal system in November of 2010 at the time of a hard drive crash.  The only advantage XP has (for me) over Win2K is ability to stream Netflix and run other media content that doesn't work on 2K ... but I can also stream Netflix on my DVD player and Roku.

I have one Win7 system, which was provided in May 2001 by (and belongs to) a different employer.
 
I joined a group medical practice last fall. Still in my same one-doctor group, but now we are employed/managed by the group. Prior to this move, we did all the insurance claims and billing on an in-house basis, whereas many of my colleagues had outsourced it. The billing system we used was the 2005 version (we began with the 1998 version, then upgraded to 2001 version and finally to the 2005 version). In 2007-8 there were substantial changes to how claims had to be submitted, but the electronic clearinghouse that handled our claims had written patches so that my 2005 version would comply with 2008 regulations. So we were able to make the 2005 version work without shelling out thousands for the new version.

More importantly, the 2008 and up versions run only on Win 7, they won't run on XP. Don't ask me why. And the 2005 will run on XP but no later versions like Win 7. That is the reason I bought the XP disk when I did---to ensure I'd have a way to upgrade or downgrade a computer to Win XP so I could continue to use the billing software.

Now that we are using the group's new system, we still have to keep one local computer with XP running, which in my case is the computer that was the file server for our old system. We probably need to keep it running for another seven years, even though the Accounts Receivable in the old computer is all paid off, because we could still be asked for information from the old database:

1. Patient in an accident and their insurance wants to see a ledge of when the patient was seen, how much was charged/paid, etc. This would be if the insurance is going after a third party (say you are rear ended and your doctor treats you, but then your Blue Cross goes after the other motorist's car insurance to recoup its costs).

2. Attorney requests for information in the case of a patient in an accident or Workmans Comp situation.

3. Malpractice suit: you may have to generate a ledge of charges re: the patient

4. Divorce/child custody proceedings: attorney may need to see a ledger of parent's or child's medical expenses over an extended time.

So we plan to keep that computer running for another six or seven years. It's a Dell and so there is a system reinstall disk for it, and we have the install disk for the software. (I bought the XP disk in 2008-9, and bought the Dell in 2010, but to restore the Dell you pretty much have to use the disk that came with it).
 
I'm going to apologize for threadjacking, but I thought I should put in a word or two here about these legacy systems.

For a lot of businesses, running hardware older than 5 years old starts becoming a liability and a serious risk. For a few reasons especially:

1. The manufacturer stops supporting the hardware by not supplying parts anymore. Either that, or replacement parts start becoming expensive.
2. Any service contract renewals for that hardware start becoming quite expensive in relation to the value of the hardware.
3. The efficiency of the hardware comes into question. ie. The newer the hardware is, the more "work" it can do in a shorter period of time.
4. Old hardware also has issues. Batteries go flat, hard drives suffer from mechanical failure and electromigration can cause the hardware to become flaky.
5. Unsupported software is a massive liability to any enterprise. Ensuring that the systems are kept up to date also means that all of the software must also be kept up to date as well, which leads to supportability and maintainability.

To DADoES... In this modern age, there is no excuse to be running that software on such antiquated hardware when it can be virtualized and running on modern hardware.

Still, when a software vendor becomes non-existent or stops supporting their software, it is time to start looking at other vendors who will support their software, otherwise this is a massive liability when support is required.

I will admit that some systems are "Fire and Forget", but when it goes down, either due to a hardware or software issue, who can they call?
 
I am reminded now of a story...

This one department in a small town was running an IBM System/34 Minicomputer which they had installed in the late 1970's. This system acted as their accounting system and pretty much did all of accounts payable and accounts receivable as well as payroll and a few other miscellaneous functions..

This system ran continuously right up until the very late 1990's.. by that time, this system was costing the city around $30,000/month in support contracts. Despite the fact this machine was around 20 years old, the staff continued to use it because it "Did the job" and worked well for the City.

A new lead accountant was hired on in the late 1990s. One of the first things that person did was a "Zero Budget", which means they would start from square one and determine where the money was going. Imagine their shock and surprise when they found out that they could purchase multiple copies of Windows NT 4.0, Microsoft Office 97 and a bunch of IBM Thinkcenter PC's for the same as one months worth of support contracts, then spend another months worth of support contract money on an accounting package.

It doesn't stop there though.. The new accounting package was much more flexible than the old one, more complex to use but this also came with support as well for a fraction of the price. Not to mention, the company who wrote it was still in business. :)

The sad part was... when they ran the account reconciliations, they were used to it taking close to 12 hours for it to run. This was considered to be status quo. Imagine finding out that by using the new accounting package, the same data could be processed in less than ten minutes.

Now can you imagine for a moment.. That old System/34 had about as much processing power as a 20 year old PC, yet used a 240 volt circuit, sat in an air conditioned room with raised flooring and nobody knew when it would finally die. What if it did? Imagine the many thousands of dollars in lost productivity and downtime that would have happened.

This is primarily the reason why anyone in IT wants to keep everything current and up to date. Old technology can end up costing more money than people realize. Of course, this is an extreme example!
 
I own the software from my 2005 version (no annual license, I own it 100%) but it will not run on any version of Windows after XP. I don't need software support, partly because no changes are being made to the database any more, we just need it to generate reports upon request (a patient ledger, usually). If it ran on 7, I'd put it on a 7 computer and restore the database, which is backed up after each use of the computer. In our situation, the database is no longer a daily driver but rather something we may use once a month---but will need to keep handy for six to seven years. Although we have a new thin client network all over the office, we still need to keep the "legacy computer" (only 1 1/2 years old, and running XP Pro) for access to the old database, plus as a means of scanning documents that are not going to be entered into our new database. Examples:

1. Patient "gualin" has been a patient for six years, this week is the first time he's been in since we went live on the new system this month. All of gualin's old paper records are scanned into the new database and the paper records can be shredded (but in reality, we are hanging on to the paper because it's easier to reference than wading through 300 pages of PDF images).

2. Patient "gualin" moves to a new city and his new physicians request the old records. His last visit was prior to our migration to our new system. In this setting, we don't want to scan the records into the new system. We make a local (not on the network) PDF scan of the records, burn them to a CD, and mail the CD to the new physician. Since the thin clients don't have hard drives and cannot accept an external hard drive (maybe they can but I don't have admin privilges), we still need one local computer with a hard drive for this purpose.

Since we already have to keep that computer (the former file server for our old system) going for old database purposes, at least it serves two functions. In the USA, paper medical records are supposed to be maintained for ten years after the last visit, after which time you can shred paper records. Of course, XP won't be supported in a few more years, but we can disconnect the computer from the internet and use it just for old database and local scanning purposes.
 
I still use a word processing program that was discontinued in the 90s for heavy duty writing projects. It is the best program I've used--it has the features I actually need, but it's not bloated with features. It's fast and stable.

Frankly, the fact it's unsupported is irrelevant. I have used this program nearly 20 years now, and it has proven itself quite reliable. I have long since found all the little problem areas, and know how to address them.

Many people using Microsoft Word (the "industry standard" word processor that we're all supposed to have and just adore because it's what every one has) can't say the same thing. In fact, two years ago, I got treated to a diatribe about Word. The woman worked in a law office, and they had Word because it's what everyone uses. She positively hates that program. One issue, ironically, comes through support. She said she would battle Word for hours getting a legal document to lay out correctly. Then the next day, some patches install in Word, and the document would fall to pieces.

I do regularly look into the possibility of migrating to a current program. I have shifted to using gedit (plain text editor) a lot. Maybe various other programs that can run on my current system will evolve in time to be satisfactory. But to totally update to modern software TODAY would require a huge cash outlay. Mainly because the only programs I've seen that might fit my criteria are OS X native. My current tech budget doesn't run to a new Apple computer. It also doesn't run to replacing said Apple computer every three years to allow me to keep running the current, supported version of OS X.
 
This might bring about my two cents...

In certain situations, replacing hardware may not be necessary. In the case where the cost of maintenance is very little (not the huge $30K or so required for the old IBM system), i.e. to keep the system network going, or ensure everything works still, I think running older stuff is fine - especially if there are no real improvements in newer versions or no security risks involved running older systems.

The above reason is (probably) why one of our local supermarkets (we have a few) still have Win2K systems. The fastest checkout operators can't run to fast for them, they very rarely have issues (except when the EFTPOS/Credit Card machine refuses to talk to the XP Eftpos PC) and they aren't vulnerable to security risks, since they aren't connected to the internet in any way!
In fact, one of the counters recently got a new EFTPOS/Credit Card scanner. No compatibility issues, and runs far better than the others.

In a supermarket, replacing hardware might be needed if the cash-drawers wear out - i.e. rollers or springs go bad, which happens to be the case at the local Win2K store... Some of the drawers have had the richard sadly, so they don't open 100% and make terrible squeaking sounds as the stop 3/4 of the way open!

At that store, the stock management, EFTPOS PC and some other pc all run Windows XP, since they probably have communication to the outside world. Whereas the checkout systems don't need upgrading, and Windows 2000 isn't insecure in any case (just as good as XP, just without the fancy Multimedia and colours).

I also knew of a school who were the last in a rental chain for lower end computers. They had 2000(ish) PC's that were still fine and could handle everyday tasks (except when students started bringing their own thumb drives). They ran XP. Some older systems that were being replaced by this were being kept, as they were P3 systems, and would get bigger HD's, more RAM, cleaning and maybe a new disk drive. I got one of these computers, and it ran like a champ off the network (loading scripts etc at startup just doesn't do it for older systems). Sadly, I've gotten rid of it now, since i needed more room and couldn't keep 3 PC"s (two desks + 1 laptop!)
 

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