I'm not sure how much it would matter in the later years, but our current pre-school is basically around the corner (after day-care several miles away), and I love it! For drop-off and pick-up we just up and run, you can ask other parents to help out easily if you have a short-term scheduling conflict and we've been able to have playdates for our (socially struggling) DS simply by having people walk by and asking them to drop in (and kids always want to because our messy, full-of-toys yard looks so interesting!). I can tell DS feels "ownership", too. I also like that there is a community we feel part of (it's church-based but the whole neighbourhood sends their kids there, Catholic, Protestant, Muslim, whatever), even though I don't think I'll make my best friends there, or haven't yet.
I'm pretty sure it isn't the best environment academically I can offer him but other options (language immersion, Montessori) were just too much of a hassle transport-wise and also, in the case of language immersion, financially (to be clear, it is play-based/developmental pre-school and so would the LI have been - I wouldn't have wanted an academic pre-school, just a little more structure and challenge than the current one has to offer). For pre-school, the nearness and community aspect outweighed the academic aspect for us.
The transition to first grade will have us re-evaluate our priorities, because the academic aspect will of course be more important then and kids are more discerning about making friends...there is the uninspiring public elementary around the other corner as it were, a very well regarded Catholic school next to my husbands workplace a few miles away,a very well regarded Montessori yet a little further...and 5th grade will be yet another transition. I don't envy you -I would feel overwhelmed if I felt I needed to make this decision for NINE years - how would you want to know your kids needs in nine years? Are you sure there isnt' room to take this one or even a few years at the time and reevaluate as things change?