IMO its really not a bad idea. I can get a better read on my hometown Red Sox than the average fantasy fan. Last year I was first to the WW for Will Middlebrooks and first to cut Jon Lester from my teams. As far as overpaying goes I see David Ortiz as a player who can still hit with the best of them, and I am confidant he will be ready to go full 'speed' in early April. Pedrioa batting third is also intriguing and he could put up 1st round numbers if Ellsbury, Ortiz, Napoli and co can stay healthy for 80% of the year. I do plan on having these guys on my teams this year if I can, they are determined to show last year was an aberration, and Napoli is out to prove he can be a healthy asset at 1B. Ellsbury is the only one that I think people still overrate. I wouldn't expect any more than a dozen home runs from him and his speed hasn't been the same since his last injury. Should score a buttload of runs though.
As far as overreaching to get someone you love, let them do it, but i wouldn't reach for a guy just for trade bait for later. They open the door for you to make a better team. I did a snake draft the other day and got Braun at #4 because someone wanted to use a #2 pick on Verlander.