We've been in DS going on 5 years.
Pros:
- still has the small town feel (for now)
- great breweries, wineries, distilleries
- growing restaurant scene
- awesome schools
- far enough out of Austin but still accessible to Austin
- fairly good access to services like high speed internet, etc.
- dark sky status which is kinda cool
- HEB
- cool state and county parks: Pedernales Falls, Reimers Ranch, Enchanted Rock, Hamilton Pool, and even Lost Maples/Garner State Park not too far
- not bad for commuting to San Antonio down 281
- still let you put your groceries in those evil plastic bags
Cons:
- it's growing way too fast
- zero affordable housing. Hard to find a house under $300k (this comes in to play if you have retired parents that you want to bring along one day as well)
- not much ethnic diversity in the school system or people in general
- being invaded by austinites and Californians, which can be seen by the transformation on the DS Neighbors page on Facebook as well as the number of Beto signs starting to show up in yards
- 290 is a death trap (I'm scared to death of my kids driving 290 when they reach driving age)
- 290 has little capacity for expansion without using eminent domain, not sure how all these cars will commute in 5 years
- have to drive to Austin or bee cave when you need something like fishing tackle or a present for a kids party
- for some reason there's an insanely high volume of dentists, car repair shops, and nail salons, and I have no idea why.
- lots of one lane roads like Hamilton pool road, sawyer ranch, rr12, with jackass drivers that tailgate and flash lights because you're only driving the speed limit
Honestly, I really like it here. When we lived in circle c, I got tired of neighbors and a lack of privacy (I suffer from cranky old man syndrome). Now we're on 4 acres and nobody bothers us. Of course land is harder to come by these days and at a premium.
The new houses are really nice. We have some friends over in the headwaters subdivision, and while it's smaller lots, the views from many of the lots are amazing, and the amenities are great.