What to do (Hoof Woes)

Suggestions? I obviously need to get this dealt with before I ride him.

Ask your farrier what he/she would recommend.
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Yeah, probably should have said - I will be calling farriers for advice but wanted outside opinions too. I don't have a farrier that I trust yet so I'd like to have 'reference points' in case the ones I ask are just after a profit/easy fix.

Talk to other local horse people and see who they recommend in your area. Not all farriers are out to make a quick buck, and get a certified farrier.
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Pics or no pics, you already know he's in pain. Shoes with pads would probably make sense for at least until he's comfortable again. Hoof boots are not logical for an ouchy horse in that they are not supposed to be left on 24/7 and you're guy sounds like he needs full time help.

Thanks MBP, I hate recommending getting a horse shod on this forum because of all the barefoot gurus, but seriously, if the horse is tenderfooted, give him a set of shoes.

I don't think this forum is that far left or right where shoes are concerned. While most of us like the idea of barefoot, many of us have tried it and had to go back to shoes since our horses were ouchy. If anything, over the past year or so I can think of several regular posters who would never suggest shoes in the past, but seem to be moderating their views in recent months. I like that, on this forum in particular, in the end everyone tries to do what's best for their horse.

I'm thinking the barefoot movement has finally made its initial run, all the incorrect of overstated info has worked itself out, and what is left is now a well intentioned objective with realistic expectations of the eventual outcome.

Put shoes on him. I don't even think you need to invest in pads. Shoes will do wonders for him.

At least it looks like he has a nice frog and no thrush!

I am going to "sound like a broken record" (no one under 45 knows what means) BUT:

Diet WILL help toughen his hooves up. He may never be able to be ridden without shoes but diet helps.

My 25 yo TWH has always been flat-footed and very tender; he always wore shoes.

He was diagnosed Equine Metabolic Syndrome in 2007 and his diet under went a major major change.

About a year after the change to a very low starch diet, I noticed he went gaiting across the gravel drive without missing a lick.

I decided to bridle him and go down the road to see what he'd do barefoot on the road. To my surprise he went down the road at a pretty good lick and stayed in stones in the center of the road.

I would still shoe him if we were hard trail riding but changing his diet to as low starch as I can get it, has surprisingly strengthend his soles to allow me to ride him barefoot for all the more I do around here.

Both the vet and the Trimmers told me that, while all my horses have great hooves, the best hooves in the barn belong to the two with metabolic issues

Hopefully you find a farrier you can trust

An no, we are not anti-shoes. All my horses are barefoot because (A) I can't ride anymore (B) two of them never did need shoes to go "4-wheelin'.

If I were still riding like I used to, the other two horses would take turns having a set of shoes put on. I would rotate them to force me to ride them both

Anyway, along with hoping you find a trustworthy and knowledgeable farrier, at least give some thought to a change in diet