Since I may be arriving at night and from Houston, would flying into marfa be any more or less of a hassle than alpine?
The hills are certainly deserving of consideration, although for the most part it is not a huge concern even at night. (Add weather and my answer changes significantly.) There have not been a huge number of hill-hitting accidents there, although I recall a story of one decades ago in imc.
An erudite pilot friend of mine said there is great comfort in simply performing the iap to such airports at night if able - and that makes great sense to me.
The Alpine hills are a few miles from the airport, east, south, through west, mainly. When I arrive from the east, I stay at 8.5 til past the Glass Mnts...til ~5-7mi from BWR or TIFME then down to 7, and turn inbound from about there. If there is a moon you may not have to do any of this but it is <1/2 and waning after the 12th.
Marfa does have a little more clearance but night would not deter most folks from going to Alpine if that's their destination. However, if your comfort level says 'Marfa' that's great too.
A go round on 19 or 23 at Alpine at night is ok, as long as you have the climb rate and don't lollygag and wait miles to make your turn back to the north.