I haven't seen a specialist for years, but I've done trial and error on my own. There's three things that matter when it comes to deciding on a shoe: weight, cushioning and drop. I prefer lower drop, lighter shoes. It has to have some cushion, but not so much that my ankles can flex laterally even more than they do. So far, the New Balance Boracay is my favorite shoe. Plenty of cushioning but with a wide enough base to stay stable. It has a 4mm drop. I think my next pair will be Hoka One One Cliftons, but my god, they are ugly. The biggest thing that helped was fixing my form. Going from a heel-to-toe strike to a mid-foot strike, straightening my body, and increasing my cadence all put less stress on my body while running and made it a more pleasant experience. I think I just reached a weekly mileage that I may have mentally and cardiovascularly ready for, but my muscles and joints weren't.