Thunderroad

As part of our trip to Yucatan next month, my wife and I will be arriving and departing from Merida. We arrive late on a Thursday night and overnight in Merida, will be in Yucatan for about 10 days, and then overnight in Merida again on a Sunday night before departing flying home from there mid-afternoon the next day. I could really use some advice about car rentals there:

1. I've read that driving around Merida can be difficult and confusing. Despite the schedule I've outlined above, which involves overnighting there our first and last nights of the trip, would we be better off simply picking up the car at the airport the day after we arrive and dropping it off there the day before we depart? For what it's worth, we've driven in several foreign countries before and have traveled in many developing countries, including Mexico (and I realize driving varies a lot among countries), and have driven in a few (but not Mexico).
2. We're still finalizing our hotel(s) in Mexico, but options include Luz en Yucatan, Rosas y Xocolate, the Hyatt and the Intercontinental. While opinions on these are welcome, for the purposes of this post I'm particularly interested in whether any are well-located near car rental outlets.
3. Is it possible with rental car companies in Mexico to pick up the car at an outlet in Merida and then return it at the airport, without lots of extra hassles and charges?
4. I'd welcome any recommendations on car rental companies, including ones to avoid.

Thanks for any help!