One thing to remember specifically with high quality leather boots is to keep up with the maintenance. I personally have a pair of iron rangers I use for work so they've gotten a lot of use and if I slack off it will not work out in the long run.

One metric I use to decide if a price is right is to divide the expected lifetime of the thing by the cost. $800 Nick's vs $70 Converse: 20+ years (with proper care) vs 2 years (maybe?), So cost/yr is $40 vs $35 which makes the initial gut punch price much less painful but the remaining question is if you trust yourself to put in the effort to properly take care of the boots in a way you (or I for that matter) would care for a pair of Converse