Tough one - I don’t have a hard cutoff, but I’ve certainly started to slow down on buying retro games. I’ve spent over $200 CAD on a single game in recent memory (2022?), nowadays I wouldn’t really want to go over $100 CAD.
I’ve also been reevaluating and selling off some of my collection whenever I can buy ports / digital versions of some games (eg: Chrono Trigger, bought on Steam and sold my loose SNES cart, Xenogears bought on PS3 and sold my CIB copy, etc).
I only focus on two retro systems - SNES and PS1 - and I don’t really play on OG hardware anyways (Super Nt / Pocket for SNES, PS3 / Vita for PS1), so I don’t mind “owning” digital and ultimately downloading roms if necessary.

I guess the main question is where do you draw the line for “somewhat newer stuff”? 5th gen consoles only (and then which one) or even newer?
And what screen size are you looking for?

This is awesome. Radiant Silvergun isn’t my most played shmup to date but it’s definitely so so unique, I really enjoy it.
I certainly think romhacks/patches are a major benefit to older gen titles and I’m somewhat concerned we’ll lose that with newer gens.

I picked up quite a few games - Deathsmiles, DoDonPachi Resurrection, Mega Man X Legacy Collection, Mushihimesama, ProtoCorgi, Star Wars Galactic Battlegrounds Saga, TMNT Shredder’s Revenge and Ultrakill.

I’ve only played ProtoCorgi so far and I kinda love it - I mean, you’re a corgi, barking or shooting lasers at various enemies in space, what’s not to love?
I’ve already played most of the other games before and wanted to own them on Steam, except for Ultrakill (and I’m really looking forward to that one).

You’re absolutely right, only the AGS 101 is backlit, my mistake!

Many options exist, depending on your budget:

• IPS screen mod for your GB, these are usually not too costly iirc ($60 USD?)
• GBA SP (AGS 001 is frontlit and AGS 101 is backlit), around the same budget for the former, the latter is more coveted and expensive. (EDIT - initial mistake, the GBA is not front/backlit)
• Open source cartreader to dump your carts and saves (and play ROMs wherever you want) - no idea about the budget tbh
• Analogue Pocket, it’s great but very likely overkill if all you want to do is play some GB games ($220 USD)
• Depending on how comfortable you are with downloading ROMs (and how ethical you feel that is, given you already have the games), you could just do that without spending a penny since GB games have been preserved and are easily accessible.

There’s also a handful of other options (GameCube GB Player, SNES Super GameBoy, etc), but that’s likely more consoles and accessories for you to purchase so I didn’t mention those in detail.

That’s mostly true, except for games made specifically harder so that you’d have to rent them multiple times (eg: ActRaiser 2 NTSC-U/C / SNES is much harder than its NTSC-J / SFC counterpart).

Disclaimer: I’m about as inexperienced as you are (and ended up giving up on CRTs for the time being, but mostly for lack of space tbh).

With that out of the way, my research from a couple years ago netted a couple of results, which might or might not be relevant to you (and I’m guessing you could have already found those), depending on where on the globe you are located.

• This person in the Bay Area, who also happens to manage the super useful CRT Database website.
• This person in the Lower Mainland.

If those two are not relevant to you, you might want to check your local CL / Kijiji / FB Marketplace / local equivalent(s) for potential listings.

Otherwise you could certainly YOLO it with the Trinitron since it’s well documented, assuming you feel confident enough around high voltage and are equipped with the necessary tools to discharge the tube, etc. From what I’ve seen it’s not as bad as it seems, as long as you you’re careful and follow the right steps/tutorials.
Do you have any spare PCB / whatever lying around you could use to practice soldering with? Components on CRT PCBs are indeed not so small, so I don’t know what sort of prior experience you have with soldering, but bigger components = easier to solder (as long as you use a bigger tip on your soldering iron, and feel free to use flux / add fresh solder).

• Wii, you’d be perfectly fine either way, you’ll be able to get 480p 2x on the OSSC or 3x on the 5X.
• PS2, you’d really benefit from the 5X for a vast majority of games, which output 480i, as the deinterlacing on the 5X is much better than the OSSC, here’s an example on GT4, and you’d again get 3x (1440p) vs 2x (960p) on the OSSC.
  You could try and force 480p via GSM otherwise, if your PS2 is nodded, but I’ve had pretty poor luck with that method so I wouldn’t recommend it.
• PS1, that’s debatable, for most games you’d be completely fine either way, but there’s a fair number of them with res switching, which the 5X tends to handle better / without any delay vs the OSSC, so if that matters to you, that could be another pro for the 5X.

You’re kinda in the perfect “target demographic” for the 5X with a PS2 in a way, but it’s a matter of how much flickering bothers you or not, and whether or not the higher output res, more features, etc, is worth the price or not.
Again, both options are absolutely great and you wouldn’t go wrong with either!

Are you using scanlines per chance? Because otherwise the amount of flickering produced via bob deinterlacing is extremely distracting tbh.

This will be dependent on a few things:

• What’s your budget?
• What consoles are you looking to play?

I can personally vouch for the OSSC as a great entry point, however there’s a caveat - if you’ll be mostly playing PS2 / inputting interlaced content and you have the budget for it, you might want to consider the RetroTink 5X, as the OSSC’s bob deinterlacing is not up to par IMO. The 5X is well worth it for that reason alone, otherwise they are both great options.

Assuming it’s nothing to do with your Dreamcast’s laser (in which case you might need to adjust it to get it going, but realistically replace it altogether), have you looked into getting the disc itself resurfaced?
If this hasn’t been done before, this would likely be the first thing to attempt before considering getting a new copy tbh. Many local game shops still have the machines for it and can do that for very little money.