I'm considering putting the Windows version of Script BASIC on the shelf until I have time to be a proper maintainer. I'm still on the fence if 32 bit is still worth investing in.
I'm curious how popular VB.Net is today and are companies developing custom apps like they did with Classic?
At one point, VB.net was popular in the corporate world because of ASP.net, but with the emergence of Node, Docker, etc, Enterprise devs have moved away from it (based on what I've seen, your experience may be different).
At work, we had an important legacy VB6/SQL application that had major issues working under Win 10 (My team and I came up with various workarounds, but with each security update that MS released we had to come up with new workarounds. The main issue was 32bit OCX). The decision was made to re-write it, and VB.net was never a real contender. The application ended up being redone in C#.
As to 32 vs 64bit: My choice would be 64bit. If we were talking about a compiler that emits ASM, I would say stay 32bit (64bit ASM is a very different beast) but for an interpreter that supports interfacing with external libraries, 64bit is the way to go since it's getting harder to find up to date 32bit dll's for some major libraries.
Just my opinions...
AIR.