Here's my humble opinion, based on what I consider to be current market. I'll stick to Vintage Guns, generally made before WWI. I divide'em into "Tiers", based on price. Generally, I'm referring to restoration guns, in 15% condition or less but absent of egregious faults such as severely cut-down barrels and stocks, missing pieces, and tubes honed down to the point of being unshootable. This list is also what I've seen most available over the last few years. In each tier I'll list the more desirable guns first. If you can find a higher grade within these ranges, it's an even better deal. You won't find these prices on the internet or from a Dealer, but usually at local auctions.
Tier One. $250-$400, (depending upon condition)
Remington 1900, preferably a KED
Remington 1889, Preferably a Grade 3 Damascus, but the Grade 2 Twist is nice, as is the Grade 1 steel barrel gun.
Baker Batavia Leader.
Ithaca Field Grade guns, (Pre-NID) preferably with Twist or Damascus tubes.
Other Twist barrels guns made by smaller companies such as Syracuse, NR Davis, Hopkins & Allen, etc.
Crescents
Belgian low-grade guns, but you can sometimes find gems in this category as well.
Tier 2, $400-$800.
Parker PH and GH.
English Hammer guns.
Tier 3, $800+
Parker DH, and higher-grade guns in general.
This is a very simple guide, and I'm sure others will contribute their views.
Regards
Ken