Some of those boots cost more than my Tour Master Solution WP boots! I used to wear my military hightops with steel toes but found out the steel toe insert was more dangerous for mc riding than safe... in an accident the steel toe insert can be levered up and cut off the toes!!!
The mentioned ankle protection is another thing to consider. The heavy leather hightop work boots will do well for protection against sliding on pavement or small impacts, like from rocks and such, but won't protect from more substantial impact as in a crash. My TM boots have some ankle armour for that.
Being waterproof is good, but is a personal preference. Some riders feel that being waterproof will make the boot hotter in hot weather. And it does, a little. I prefer to combine my gear for as many conditions as possible so I don't have to buy many jackets, boots, gloves, at least not any more than I really have to. I find my TM boots work well in heavy rain, cold, warm/hot, etc. Sure, the feet sweat a bit in hot temps but that's going to happen a bit anyway. Many mc boots have a plastic toe cup that are much less likely to cut your toes off but will protect them. My former boots, also from TM, did just that when I low sided. There was a gash in the top center of the right toe area of the boot, but my feet didn't feel a thing and no injury even though the toe cup was broken in half. Oh, and road rash on the side of my boot but I didn't feel that either.
Take a look at some of these boots where I get most of my gear at Motorcyclegear.com
Boots, like everything else with a motorcycle, are a matter of personal preference and everyone will tell you their own opinion about what is best. This is mine.
Oh- and mc boots usually have a reinforcement patch over the left toe to aid in wear from the shifter.
