I even heard of a port of firefox to amiga os and that's pretty sweet for something this old (I'm running tenfourfox on my old 2004 ibook g4 and that's pretty neat too)
Timberwolf. No longer being developed. Again, you're going to have to spend a heck of a lot of money to run that on a classic system:
https://en.wikipedia.org/wiki/Timberwolf_(web_browser)This is a debatable topic, again just IMHO Chris's version of NetSurf is the most advanced browser for classic systems, but it's slooow and needs a lot of memory. Ibrowse is probably the best balance of speed & compatibility (I use that term "compatibility" pretty loosely, as you're not going to be updating your Facebook from it, or anything like that). I've found it's mostly good for reading news sites and downloading from Aminet. It hasn't been updated in over 10 years but occasionally a whisper comes up about some kind of update for it.
As for modern screens, I was thinking of looking around for an amiga monitor, unless they're not worth the price?
Not to me, but some people swear by 'em, especially for retro gaming. I guess if you like using a flickery 13" screen and pretending like it's 1992 all over again, have at it. LOL. But if you want to run modern applications at high resolutions, they're not going to cut the mustard.
You might want to think about this plan a bit and try to figure out which way you want to go. Do you want a stock or mildly expanded system, with an old school monitor for retro gaming, or do you want a "pimped out" system capable of playing Quake, Timberwolf, etc.?
Also, what's your budget? Not trying to pick on you but you mention "minimum wage" and "barely being above welfare"... a high-end classic Amiga system can easily run $1,000+, depending on the parts you chose for it. Maybe an A500 or A600 would be cheaper for you, and with those you'll have the option of using one of the new Vampire accelerators, which give improved graphics and speeds exceeding even the 68060. No idea when (or if) the Vampire 1200 will ever come out.