We can probably help you with the Appalachian Trail part of your hike planning. There was a poster on here named Gershon who was getting into road walking but he has not posted in several years. You could try messaging him.

Off the top of my head, stealth camping and hammocks probably don't go together. Stealth camping runs the line of legality and a high potential of upsetting people. I wouldn't think you would want to strap on to trees for that. Typically you want to be in a small bivy or tent under the bushes.

You mention hiking boots. Most around here have given up on heavy hiking boots and gravitated towards light weight low top trail runners. Your feet move more than most any other part of your body while hiking. Losing weight there is very beneficial.