I know that when you apply for mayor and its accepted, you get your own piece of land for the town (obviously). When you get the land, does your /home automatically reset to that land?, or is there a different way of accessing that chunk of land?
Well, when you set your town up, you do it manually by setting your posts... Therefor, you'll be in your town. It'd be wise to set your home there while making the posts.
There will be no automatic way of getting to the region. You will have to set a home, use a nearby portal, or apply for a portal or warp.
Homes do not automatically set to anything - it is all manual with /sethome. However, if you protect land and become a Mayor, you can use /rg i <townname> to find co-ordinates of the town corner(s). Only way to get to a town other than walking is by setting a home there, having someone go there and teleport to them, buying a warp for the town, or buying a portal for it.