There are sites that will give you an idea of reception. You can even put gps coordinates and elevations, that works the best. If I can find the sites I'll pass it on, but chances are the antenna sales sites should provide a link.
As FFJ pointed out don't go cheap on the cable, and especially, make sure the connectors are on properly.Same with a signal booster, if needed. Thats something you can add later, usually does not need to be done on the roof.
Rotor- use the sites above to see where you're channels come from. Don't buy a weather master or channel master. I did, lasts about 14 to 18 months. Check 'em out at radio shacks website, and check out the consumer ratings. I plan on going up on the roof and turning my antenna(when I put the new one on) and checking it then. I've got stations in opposite directions, and they may be on the weak side. If one direction doesn't work, I'll lock the antenna in on the stations I get and leave it. I've had an antenna for 10 years, and its all stove to c@t sh!t, from the wind. It is a miantenace item. I'm on the outer fringe of reception, need to keep in good shape. If you need a rotor, google "Norms Rotors", they are a little pricey, but they'll last. Call and talk to "norm" directly.
What I've learned is the bigger the antenna, the better reception. Makes sense. I don't think I paid more than $100 dollars for the biggest and the best. 10yrs ago, it cost me $350 to have antenna,bracket. cable, booster, rotor(piece of crap) put high on top of roof.
But he told me he won't go up there again, too high.
You mentioned barn, might be a good spot for an antenna, just make sure the cable will carry the signal if it's a long ways away.
I've got the digital box, and right now can't get anything. But I used to get analog"wall to wall"(bangor, P.I., and canada) but over the years the signal got weak, damage to antenna, plus the rotor not working. My best channels had been from New Brunswick Canada. If I don't get digital, I'll turn into a Canuck. They've got some decent stuff over there, and good prime time comedy specials. You Hoser! Plus good beer..or so I've heard.