As per other's posts, need more info & pref hoof pics(see link below). Re possibility of laminitis/founder, unfortunately it is a distinct possibility - could be before you got him too. Re diet & lami, check out Equine Cushing's and Insulin Resistance Information & Katy Watts | Safergrass.org. Also hoofrehab.com is a good online resource IMO.
Re diet, I would personally run it by a nutritionist or use a program such as feedxl.com. If you're feeding something like corn oil, it's best to feed it little & often over a few feeds rather than once daily. What's the aspirin, lysine & electro dex for? It's possible ongoing aspirin could lead to laminitis, as these type drugs damage gut lining & allow toxins into the blood.
I would consider getting an equine vet & getting xrays done. *Make sure his feet are marked for rads - eg point of frog, dorsal wall. I would not be inclined to put shoes on him & if I did I would be ensuring they were well packed/padded. Instead hoof boots are a good option to provide full protection & support to his soles without the 'cons' of nail on rims.