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This might help as a starting point...
I hope that you do not find me to arrogant. But what you ask for is probably not what will get you the best advice:-)
If your FileMaker 8.5 solution is build without relying on a lot of plugins it will probably be a piece of cake to convert it to FileMaker 14 and you should expect it to work like a dream and you can start using the many new functions from 9, 10, 11, 12, 13 and 14!
- Using IWP?
- Custom Web Publishing?
- MS Windows?
- iPad/iPhone ... FileMaker Go (future, of course not 8.5)
FileMaker 14 is supporting Mac OS X 10.9, 10.10 and 10.11 and I would suggest that you decide to go for the newest version of FileMaker, whatever that may be when you make your decision.
I do quite a lot of work with a charity with the same situation of a limited budget and a bunch of Macs of various ages. Up until very recently, there were some of them still using Mac OS 10.6, and we were using FileMaker 11.
However, time has come to upgrade as well, and we decided to finally retire the oldest Mac minis running 10.6 that couldn't take 10.7, and replace them with newer ones off of eBay - 2012 Mac minis are a nice buy, and capable of running latest Mac OS X 10.11 and latest FileMaker 14
This has left us with a mix of Macs running minimum Mac OS 10.7 and now mostly 10.10 or 10.11
This has allowed us to upgrade to FileMaker Server 14, and all the Macs running FileMaker Pro 13 (on Mac OS 10.7 - 10.8) or 14 (on 10.9 and newer)... Using minimum FileMaker 13 allows us to use the ton of features introduced with that version such as pop-overs, slide controls, and object visibility calculations... Although OS X 10.6 can take FMP 12, the additional features of v13 and perhaps the maturity of the .fmp12 format in v13 makes it well worth aiming for, rather than v12, which I found to be a bit wobbly at times... But yes, v13 needs OS X 10.7 or newer.
Hopefully over the next few months we will have another round of getting rid of older machines that can't take v14, so min OS X is 10.10 and all using v14 so we can make use of things like SVG button icons etc, plus the sanity of all using the same version FMP, although we haven't had any issues with Pro 13 clients connecting to Server 14 - it's mainly just the difference in supported features sets that limits things to the lowest common set.
The change from v11 to 14 was fairly painless - the main database converted from .fmp7 to .fmp12 without any problems... Believe it or not that same database file has made it's way from FileMaker Pro 4 way back in 1989! and been upgraded through the versions to where it is now... Some of the very original layouts are still buried in there too...
Good luck with the upgrade :-)
I can't say for sure, but you may get a special price for your type of organisation. Check with someone at FileMaker, maybe you'l get a pleasant answer. You may also have a look at Corporate Donations - FileMaker
If not, do you have sponsors that may help you buy FileMaker 14 ?
Versions from 7 to 11 all have the file format of ".fp7". Versions 12 through current have a format of ".fmp12". For you, this means that you could upgrade to FileMaker 11 by simply installing FM11 software. No conversion at all would be necessary. Trouble is...I doubt you can buy FM11.
In your case, my guess is you have one main database. Maybe a few, but probably just one. If you had FM 12, 13, or 14, you could open and convert the database you have in just a few minutes. It would most likely work just as it always has. Again, you probably can't buy FM12 or FM13 any more (nor should you). So...for the price of upgrading software from 8.5 to 14, your database could be updated and you'd be current.
Is this database "served", or do you share it using peer-to-peer sharing? And do check with FM Inc. regarding pricing for non-profits.