Wish I could say thet EMS was the best, but they are only mid grade as far as qualifications go. Same for Dicks or any chain stores. For the last couple years, they will agree with anything the customer says to make a sale. That said, they sometimes provide a minimal amount of training in footwear. Most are colledge kids, though. Smaller specialized shoe stores will usually provide a higher quality of assitance, but, you will pay for that.
Overall, your best will be to simply start trying on shoes. When you find one that is just very comfortable, that is the one. Most inserts are just helps for ill fitting mass production shoes. That said, try BOTH feet. And walk, and run around the store. Relace them and do it again. It may take an 8 hour day or two to pick out a set. Don't be afraid of inserts, these are recommended for long distance hikes or hard miles. But, don't rely on them. For winter boots, synthetics are good. But this is only 3 months out of a year. Double socks in regular boots are usually enough.
Pick out the lightest you can find, check them out thuroughly. Ankle supports should have a scree sheild or padded ridge around the upper to keep stuff out. Generally, they will NOT protect your ankles against sprains and breaks. A full boot, might. Mostly, the low cut boots will protect against bruising, scrapes, and punctures. Only about a half to two pounds of actual support is added, though. This will depend on how you lace them and how tight. They should weigh ~1#8 each. Give or take a few ounces…
Leather will streatch over the course of a day. So, even though your feet swell with walking, they should remain comfortable. Do not overtighten the laces in the morning, anyway. A tight shoe will really fatigue your lower legs.
Canoeing is different, as you know. Wet feet happen a lot. Good trails are not the norm in NY. But, the sections of the AT (Georgia, NJ, Pen, NY, CT, ME,) I have hiked are good. This is where multiple shoes are likely wanted. If I don't know about a trail, I take my mid boots. They are never out of place, though they might be heavier than I need. If I know the trail is good, I take my trail shoes. Both sandals and trail shoes are more specialized. Anytime, I take a pack with more than 20lb's though, I wear my boots. For a weekend, often my trail shoes.