TJ:
More $$ than you mentioned you wanted to spend, but I'll be posting a Harvey Dean Southern bowie real soon. Carbon steel, stainless guard, exceptionally fantastic stag and 100% brand new condition. With sheath from Harvey. I bought the knife from Dave Ellis, who bought it from Harvey at Blade '06. I'm not trying to turn this into a "for sale" thread, but rather expressing my strong opinion that this is exactly the kind of knife that you want to invest in as a "knife novice". If I were you, I'd go for a signature style knife from a recognized top tier Mastersmith, who is active, has a backlog of orders, doing shows and is still reasonably priced. My personal choices here are Harvey Dean and Daniel Winkler. Two very different makers, but they both meet the criteria I laid out. I'd go with a signature style, large bowie from either one, carbon steel to keep it more affordable, nice stag handle. Don't go with wood on a bowie. Okay for hunters, but not bowies. If you buy one second hand, I like the knife to be 100% mint and original. Ask the seller if there are any pits in the blade, or handing marks. If so, pass on it. Go for 100% new condition. You'll spend in the $1600 to $1800 range, get a knife that you can be confident will hold all of it's value and that, in my opinion, will probably appreciate into the low $2000's before too long.
"Up and comers" are a tough call. At least for me. Sometimes a maker just never gets real "hot". Sometimes there's an identifiable reason for it and sometimes there just isn't. Dean and Winkler are already there, still relatively affordable with nowhere to go, but up. Believe it or not, bowies are a little soft right now. It's a great time to buy. No doubt, some here will have opinions that differ from mine. Gather all the opinions and do what makes the most sense to you.
On another note, I wanted to contact you and tap into your 1911 experience and opinions. Welcome to the knife world!
Pete