He's free to waste money in Virginia, Colorado, and New Hampshire.
New Hampshire is cheap and a rather important 2nd path. It's a wise decision.
To adequately cover New Hampshire is hardly cheap - you have to buy in the pricey Boston TV market, and maybe Portland, ME and Burlington, VT to reach the northern parts of the state. Just making an ad buy on WMUR (Manchester, NH's ABC Affiliate which is technically in the Boston TV market) likely isn't sufficient. When the ad buys are fully in, I'll check what Trump actually bought in to reach the state.
If you're already buying Portland to reach Northern New Hampshire, adding on the cheap Bangor and Presque Isle, ME markets to reach all of Maine (and ME-02) isn't that much of a stretch.
Is that all still true in the days of cable/direct tv, etc.? I know you can actually tailor ads to specific suburbs in Chicago area by buying specific cable systems. I would think that would be doable in more rural areas as well.