For clarity, they aren't my client yet. I'm still trying to feel this out, and figure out how much work is going to be for me, and whether or not it's going to be worthwhile.
I do have to laugh at myself here. As much work as I do with virtualization, (xVM hypervisor) the thought didn't even occur to me to use a DOS VM. I haven't looked at DOS in more years than I care to admit...might show my age lol.
I wont at this point go so far as to say they don't need SBS anymore, as I'm still trying to find out what all they are using it for. The problem is, they were given a server that was underpowered (and overpriced) for SBS to begin with. That machine is now 5 years old, and I don't think it has EVER been rebooted. At this point they need to start over either way. SBS or otherwise.
Some of the other problems, is that they have daily backups that are SUPPOSED to be running to a remote site. Nobody there knows how to check the backups, how to make sure the mirrored array is still functioning properly, or basically anything else having to do with the system.
They are also working on an office full of Dell computers that were likewise underpowered, and over priced.
As far as your question about updating. Apparently they tried to upgrade once, and the staff basically told them where they could put the Windows version after using it. It actually takes them longer to input the information in Windows than the DOS version. Or so I was told anyway. Probably just a matter of preference.
As far as updating to a new RDBMS...that is a hard call. Considering what his current IT provider charges him per month for service, it probably has a lot to do with the cost of rewriting the software. Although I personally think they would do much better using PostGresql for the DB, and Java for the frontend. Thats just me.
