Only skimmed the first group of replies, but inclined to disagree generally... Except Joe's comment on the farrier re boots. Oh & there's no structural or strength difference between black & white hooves.
Only definite answer I'd give you is 'it depends', as every horse & situation is different, but yes, it is entirely possible that your horse will adapt to being bare with this type of lifestyle/environment. Not just going on theory here by any means, but first hand experience.
Some of the best 'candidates' for barefoot are endurance horses, doing many miles every day. It's the weekenders & horses that generally live/work on soft ground that are the worst 'candidates' for barefoot over rough ground IME. As with us, 'if you don't use it, you lose it' and if you're not doing regular exercise barefoot on hard ground, you'll lose those calluses & your skin won't grow as quickly to compensate either. Healthy horses can generally adapt to putting out as much growth as equals wear, depending on management, diet, etc.
Now for the depends. First off, even in ideal situations, sometimes wear does indeed exceed growth. Eg. Particularly long & hard endurance rides, working longer &/or harder than the horse is used to, etc. But in these situations, boots are generally a very good option. Eg. While many bare endurance horses are barefoot during training & most of the time, they usually wear boots for big rides. Many people carry boots in a saddle bag for if/when the horse is wearing too much or terrain gets a lot rougher, so their horses are predominantly bare but booted as necessary. Boots aren't suitable for every horse in every situation unfortunately, but these days there are enough choices out there to effectively cover most bases(pardon the pun!).
The vast majority of problems with boots seem to relate to bad fitting & I'd advise a boot-savvy trimmer trim & fit your horse, to ensure they're right. There are different styles suitable for different situations & Easycare's new Trail boot is a very easy, convenient & strong boot, but being high profile is not generally advisable for more than 25 miles per ride/week. As for longevity, Easycare have tried & tested their boots rigorously & say their Epics for eg. Will last around 500 miles in harsh terrain & around 1000 miles in more forgiving footing.
So... of course, your horse may have less than perfect hooves, especially if he's been shod long term, and comfort is very important, not just for humane reasons, but if he's not comfortable, he won't be using his feet properly, in order to develop further strength & avoid/rehab from problems. So I wouldn't advise/expect your horse to come straight out of shoes & be made to go bare. By all means, see how he goes, if he's comfortable, impacting heel first, etc, but be prepared to protect & support his feet with boots/pads as necessary. You may find you always need them for work, at least in certain situations, or you may find that after some months, you're using them less & less & he eventually goes bare everywhere.
I'd start out learning as much as you can about the principles behind the practices of 'natural hoofcare' & learning how the hooves function & what factors are involved, such as diet & environment, etc. Hopefully the tread link in my signature will help you get started on that.