Looking for advice on buying new discontinued music server - would you do it?

If no longer supported with software updates I would say no, if they are still supported I would say yes if its a good deal.

+1 jond

It’s fairly straightforward to find software and hardware support for (most) servers, unless proprietary software/components are being used...which was rare (though somewhat more prevalent now).

The more important consideration has to do with how fast the segment is moving which strongly points to going with a current server. Prices have also fallen so your (I presuming) logic to go with a former "higher end" server at a now lower price doesn’t hold.

Go new and latest.

I have had Bluesound for several years and required a fair amount of tech support.  I don’t know how  much of a savings there is from an old unsupported Node2 and the current 2i, but since the Node2i only costs around $500, it can’t be that much.  I would buy the new unit and have the piece of mind that it will be supported.

Does the 2i support Roon? Use as a Roon endpoint? 

I bought discounted Node 2 devices when the Node 2i came out.  I also have a couple of their speakers.  The software is the same for all their devices as far as I know and there is a lot of information in their forums if you need help.  How good are you at figuring out things on your own?  If not very good, then maybe it's not a good choice.  If you don't mind doing a little reading and experimenting, you should be fine.