Loc: Portland, OR
I'm a west-coast hiker and have no direct experience in your neck of the woods.
To help get you started planning, there is plenty of information available out there regarding the Appalachian Trail and it may be your best option for walking the majority of the distance you are planning to cover. The best source on the web for the AT would be whiteblaze.net.
Road walking is a very different beast from trail hiking and I have no experience there. I'd anticipate that sticking to back roads or rural state highways as much as possible would be the best approach.
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.
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