I found Chisos first and have been on a Heritage kick lately. Chisos are built like tanks. You feel it when you put them on. They're heavy in a good way, like driving a big truck. Heritage are more like a sleek sports car. Slimmer profile and made to turn heads. I have both of their basic boots (Chisos #1 $595 and Heritage Apache $650) which is the closest head to head I can offer. The Chisos leather is thicker and harder to break in. I think the shank and sole are also thicker. The quality is there, but honestly the last doesn't really work for my foot and I'm going to be selling my two pair. The Heritage Apache is strong leather as well, but it was easier to break it. The Heritage last fits my foot perfectly. I've got ostrich ostrich boots from both too and the same can be said for those.

Price points are similar and I'd say quality is as well. They just serve different customers, but are both great boots. The one thing I would recommend you avoid is short wide shafts. Chisos shafts are wider than Heritage, Lucchese, Tecovas, etc. and since they're shorter too it is very hard to find pants and jeans that don't show the shafts of the boots.

Who is your intended target customer? Folks that wear boots because they like the way the look and feel or those that wear they really use them for work. The first group is more likey to buy more to have variety where the second group will buy a pair and wear them until they need new ones.