In my opinion Limesurvey v2.50 Build 160311 could never be considered "working". There was so much wrong with this version that there were hundreds of updates and bug fixes within the first couple of weeks after the release (and non of which you have applied).
In any way, I don't think anyone can give you any help or support with this version. For one, it is over 5,5 years old and has been considered depricated for quite a while now, and then everyone here in the forum that I know either never even employed 2.5x in production for the above reasons (just wasn't stable for production) and went straight from the previous LTS to LS3 once it was stable, or have long dropped it.
Personally, I would never use 2.5x for any production usage, not even the latest version with a lot of the bugs fixed. You on the other hand, you are employing the very first version of it, with none of the thousands of bug fixes employed whatsoever.
If in your jurisdiction there is any privacy law like GDPR/DSVGO, LGPD, etc. in place, if anything happens, you will be in trouble if running such an outdated and knowingly bad release of the software. You sure don't guarantee the data protection with "state of the art" and "up-to-date" software. I personally just can't understand the reluctance to move away from a really bad piece of software (I am just honest here, LS 2.5x was a nightmare) with loads of bugs to a more stable and much better software, especially as there is no license cost involved. In the time you have spent on this forum discussing how to move a really old piece of software to a new server you could have setup the whole now thing.
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I know, there might be a lot of users and surveys to be transferred, but usually you could just use a copy of the old database and install the new version over that and see if things work (and they most probably will). The only thing that will not work are custom themes and custom workarounds.
Anyway: If you insist on continuing running LS 2.5x (which - you might have noticed this by now - I highly discourage
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) you might need to run your own tests. As you don't need to pay any licensing fees, you can just setup a test environment on the new server and see what happens.
As mentioned above, I highly doubt that anyone here has touched a LS 2.50 in the last couple of years, and less likely that it was on a Windows Server / Microsoft SQL Server.
So I think you are on your own when it comes to LS 2.50 in a Windows Server environment.