Taylors will be the easiest to play, and probably most stable...but they are an aquired taste. I'm trying to save up for either one of their nylon string guitars (NS34ce)or the short scale, slot head grand auditorium (GC5 maybe?).
Gibsons have had a resugence (due in part to Sheryl Crow's prominent use of them). Martin OMs took off after Clapton's Unplugged show.
I've found that Gibsons are good to strum, not to finger pick...of course Leo Kottke used a J45 (old one) for years.
I play a Mossman (
www.mossman-guitars.com) out of Sulpher Springs TX. Handbuilt by two guys down there, Bob Casey and his nephew. (They bought out previous own some twenty years ago, who had bought it from Stuart Mossman). Mine's walnut.
Of course, some of the greatest guitars have simple pedigrees: Harmony Sovereign 1260 will run around $500 on eBay. Good enough for Jimmy Paige and Mance Lipscomb. Often called the "Poor man's Martin D18).
Check out Gruhn Guitars online -- Nashville vintage/new dealer who is an author and widely acknowledged as the most knowledgable person in the world on fretted instruments. I've bought and sold guitars through his shop and his crew is fair, honest, and to be trusted.
But there is no replacement for hands on playing...I bought a Martin HD 28 in 1980 from Gruhn and played 5 different guitars (all the same model) to pick the right one, then had the shop set up the action to suit me (it had been high for Bluegrass). People aften make the mistake of buying based on action, which is an easy fix. (Interesting note, Scott Baxendale, who was an owner and eventually owner of MOSSMAN guitars was working there at the time and did the set up on my guitar....small world).
Other greats, but not so cheap: Collings, Santa Cruz, Huss & Dalton, etc. There are a ton of small builders.
Epiphone Texan is good too (just ask Paul McCartney).
Have fun choosing, I'm envious!