I put up a message on the subreddit regarding this topic; I felt people there (assuming they're not 100% represented here) have a right to know what's been going down the past little bit.
ON THAT NOTE. I have two options on the technical side of things, depending on what servers we can find and/or how much they cost:
Windows Server
If a Windows-based server could be found that doesn't cost an arm and a leg a month to meet our needs, we'd have access to all the tech in the .Net family, as well as all the neat little extensions that have come across for it. We'd also have Microsoft support in case shit hits the fan and it'd be an environment with which I am very familiar, as well as tech with which I am intimately familiar, excepting DotVVM. The only real downside is that Windows servers tend to be more expensive than the alternatives, so monetary support would be more paramount.
Linux Server
Some flavour of Linux (maybe Ubuntu or Debian or somesuch) would be far cheaper than the Windows counterparts. Unfortunately, this would likely preclude me from using a lot of the cool shit I know how to do in .Net, because I'd have to be relegated to Mono. While Mono is mostly feature-complete when compared to current .Net versions, I'm unsure as to whether or not certain bits of tech (like DotVVM) would be compatible with Mono, as I've yet to evaluate that aspect of things.
However, there are Python-based solutions that could work fairly well. I know some of the tech (Flask, Psycopg2) relatively well and Python is easy enough to work with. The upside is that everything I'd use would be both free and open-source, so nobody would be likely to come breathing down my neck for whatever we'd be having in terms of monetary support. I'm not as familiar with the frontend tech (Flask-Bootstrap), as I'm not really much of a frontend guy to begin with, but it seems simple enough to get the basics down and I'm sure there's a community out there, somewhere, where I could pose questions when they arise.
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On the financial front, I think something like Patreon would probably be best. Merch has a lot of added fees and crap tacked on that could screw us out of a lot of potential server keeping money and we'd have to worry about copycats popping up and trying to undercut us. Something with both one-time and recurring donations would be simplest, and people could choose to contribute whatever they like. Any and all funds would, of course, be put towards the site and nothing else.
I basically owe FSTDT for finding my fiancee; without it, we never would've met. I will be fucking damned if I see it die an inglorious death to a combination of personal problems and a fucking bug.