This is definitely the right place! Glad to have you!
So I can't comment on the 90's stuff, but just so you know Bloodshot had a 51-issue series that started in 1993, and another in 1997 (probably for sure don't read that one).
First of all, I don't really think he's anything like Deadpool... He's not funny or quippy. The wittiest he gets is spewing action-movie cliches every once in a while.
Secondly, you've got three(/four) series to choose from:
Bloodshot (2012): This is your basic Bloodshot story. Big action. Big explosions. Big technology. A lot of blood and violence. Bloodshot being a brooding badass. It's written by the underrated Duane Swiercynzski and consists of 13 issues, which fit into 3 tpb's, and is all collected in
Bloodshot Deluxe Edition Vol. 1. The third volume ties in to the event, Harbinger Wars, alongside Harbinger. And speaking of.. there's an awesome Compendium coming out this summer the includes Bloodshot 1-13, Harbinger 1-14, and Harbinger Wars 1-4.
Bloodshot and H.A.R.D. Corps: So this is actually a continuation of the 2012 series. It's issues 14-23, to be exact (#24 & 25 goes back to simply 'Bloodshot'). Personally, I don't love it, but the concept of HARD Corps (soldiers who can "download" psiot abilities at will) is cool, and it's leader, Charlie Palmer, is awesome. It's all collected in the second
Deluxe Edition, as well as the really good Bloodshot #0 and HARD Corps #0.
Bloodshot Reborn (2015): This one's written by Jeff Lemire, and is really really good. It takes more of an introspective look at Bloodshot, and takes him on some pretty wild adventures. If you were to pick only one, I would probably say you should get this one. It's already collected into two deluxe editions (
Vol. 1 and
Vol. 2). Also, if you do want to start here, the excellent "self-contained" event, The Valiant, acts as a sort of prelude and is also written by Lemire.
EDIT: In case you're confused about the numbering, and because I'm bored, here's the complete list:
Vol. 1- Colorado (1-5)
Vol. 2- The Hunt (6-9)
Vol. 3- The Analog Man (10-13) [Annual #1 came out around this time as well, but is just side-stories. It's included in the second deluxe ed.)
Vol. 4- Bloodshot Island (14-18)
Bloodshot USA (this is technically volume 5, but they decided to release it as an event)
Bloodshot Reborn #0 (transitional issue inbetween 'Reborn' and 'Salvation')
Book of Death: Fall of Bloodshot #1 (this was a one-shot tie-in to Book of Death, chronicling the canonical death of Bloodshot)
4001 A.D.: Bloodshot #1 (another one-shot tie-in. It's a direct continuation from Fall of Bloodshot)
Bloodshot Salvation (2017): Written by Lemire again. This one just started, so I don't really have much to say about it. If you want to jump in to the current stuff, this is your best bet.