Save your $$ until you can do both. Pulling the heads for machining and not upgrading to 95" doesn't make a lot of sense. Look for deal on pistons and cylinders; they are cheap if you look around. Some dealers have piles of them stored and, if you know a tech or a service manager, you might pick up a set for a 5th of JD. JMHO.

 

Djl's got it. If it were me, I'd do the 95 before messing with the heads. If youre not happy with it, its not that hard to take the heads off. I know this is not what you want to hear. I also know you have discussed this on other threads and have some uncertainties... So to be honest, if it were me since I "typically' do not ride past 4k rpm's and also have a limited budget, I'd sell the 37's, install 26's or 21's and do the 95" kit. I "may" consider milling the heads for ~$120, although not necessary with these cams. Your 06 and later heads are the best stock heads hd has made. Lots of people with 05 and earlier bikes buy used 06 heads for these mild builds.

Anyway, lots of decisions, and confusion for sure. Just need to decide what you want and how much you can afford.