Personality-wise, I think I'd have the easiest time getting along with either the 2nd or 11th Doctor.
But then, I find Jon Pertwee endlessly charming. (I don't know about in-character, but of all the actors IRL, Pertwee would definately be the one I'd be most interested in meeting.
The 8th Doctor would be fairly high on my list. He seemed like an easy-going guy.
The 4th, 6th, & 7th Doctors are fun to watch but I don't think I'd ever want to be in the same room with any of them. The 1st Doctor was too cranky. The 9th Doctor was too moody. The 10th Doctor was an obnoxious ham and I'd probably end up trying to punch him.
I find the 5th Doctor boring. Plus, I'd be saddled with the unpleasant prospect of spending time with Adric, Tegan, Turlough, or Peri. Maybe I'd be willing to jump in the TARDIS during that brief sliver of time between "Time-Flight" & "Arc of Infinity" when the 5th Doctor & Nyssa were travelling on their own. But even then, I'd really just be there to try to put the moves on Nyssa.