Looking at the pictures you posted, you've taken good care of him. I can clearly see the giant ripples from the inflammation that have grown down about halfway.
Him being a bit tender after removing the shoes is probably from the way his front feet are thin soled at the toe. See those slight humps before the white line at the toe? It is more noticeable in the right front than in the left front. That that tells me, along with the deep collateral grooves (or you may know them as commissures) along the frog at the heel, that he's lacking enough sole at the toe right now, but has a slight excess at the heels of horn.
I would say he would be ouchy on rocks or even concrete right now. What I would do, is have my trimmer take the heels down a little, maybe 4 millimeters on a plane that follows that hump as if it were the p3 bone (it actually IS the p3 pressing down on the sole and is what you should base your angle off of). Only from the rear quarters to the heels would you lower it, and of course, less material removed at the quarters than at the heels.
Then, refresh your bevel, without removing ANY toe height, but keep it beveled after you trim the heels. Leavet the "humps" at the toe.The bars may need shaved off to prevent excess after trimming the heels,but that's all I would recommend right now.
For the hind feet, the heels may be just a tad long. The horn tubules are growing at a much lower angle than the at the toe, incicating some crushing of the heels, or that they are trying to run forward. Just bring them down a few millimeters. They should begin at the widest part of the frog, where it meets the heel bulbs.
Overall, he's looking great!! Once that lump at the toe disappears,on its own, he should be less tender. Right now he's simply lacking enough sole material at the toe, but that will correct itself if you keep up the good trims and protect his feet with boots or only ride in softer terrain until then. Looks like he grows fast, so perhaps within another 3-4 months, he could be completely healed. Beautiful bevel, by the way!