I have a 25db signal booster AND the digital converter. I didn't add the digital converter until this year. Having the signal booster is a must regardless.
I actually use an older DirectTV dish. I have DirectTV setup through my cell phone so that when I call, if there is service, I am able to get the support for direction and settings. I can change the direction of the of the dish to get the best reception.
like jeremy, i also use winegard hideaway, a booster, and digital converter box. i put in jacks thru the pup wall, only using a single 3/8" hole, as i thought it less destructive (and less chance of leak) than mounting an entire outlet box.
this way, just a couple screw holes n the sides of the pup - no large holes and no roof holes needed.