If the tread is still good I would put a new tube, I just did this last week, tube was $25, inner spoke liner $6. plus one hour labor. Buys you time so you can put new front and rears at the same time and there would't be no problem about mixing different tires

 

It isn't just a nail hole... it was a threaded wood screw that chewed into the tire pretty good. I don't know if it went into the tube though cause it has been a few days and the tire isn't flat. It looks low to me but I might just be seeing what I expect to see.

Here is the deal... the tire isn't bald but it has about five or six thousand miles on it. I changed the rear tire at 1500 miles for a wheel swap with a forum member that had like 300 miles on it. I just don't know if it is worth the cash for a new tube, rim band, and labor, just to have to change the tire in 2k miles or so. I'm also worried about the safety of my wife. What would you guys do? An Indy here in town has a pirelli diablo strada that he will install for 60 bucks (full install, not just mount/balance), but he wants $170 for the tire. I found the tire online though for $125.

 

I was in the same boat last week with the same concerns (wife) plus my daughter frequenly rides with me as well. I spoke with several Indy shops as well as the local HD dealer, lots of riding buddies, a buddy that works at a Discout Tires in town and all say as long as you replace the tube and patch the tire all would be safe. Yes I trusted them and took their advice. Now if its a piece of mind your after, by all means get the new tire. As far as two different types of tires on the bike, I prefer to have matching front and rear. When I was getting prices for a new tire and install one shop told me "40 bucks if you buy the tire from me, 80 bucks if you bring in your own tire". So if you get your tire from the internet be sure the shop you go to don't try to raise the labor rate because you didn't buy the tire from them.