A good friend is moving to SAT area with her husband, and it will likely prove to be the case that I will end up booking at least a couple trips a year to venture to TX to see them (leisure, so generally flexible to some extent). I use "strategy", because it has always seemed to me that non-DFW/IAH (or HOU/DAL for WN) travel into TX means you either take the longish leg to/from the TX hub, and then short hop out to AUS or SAT, or you fly down to ATL on DL and take a more split trip with a shorter initial leg to ATL but longer final leg from ATL to TX. Incidentally, my one previous TX trip was CMH-AUS a few years ago on DL, and ended up being completely fine that way. Anything I'm missing either way on the logistical side that mitigates in favor of the shorter intra-TX connection vs. connecting from outside?

Specifics that will be playing for me:
-WAS-based, and prefer DCA generally, but nonstops from IAD and/or BWI are certainly not out of the realm of feasibility, especially if UA has decent to competitive pricing on IAD-SAT. It would just be the old "is the schlep out to IAD worth the n/s vs. the ease of DCA but having to connect" dilemma, so I'm kicking the tires of best connecting strategy.

-Similar to the above, I obviously am aware of WN's DCA-AUS n/s, but I don't offhand see that being of value for an SAT trip; seems like the drive out to IAD to catch an IAD-SAT n/s would be the go-to there (I can't see WN offering suck rock-bottom pricing that it would make sense, but hey, maybe!). For AUS travel, seems like the best bet (pending fares).

-I really don't have any strong feelings about a need to fly any particular carrier, so it's honestly just seeing if one way works better or not. I recall the old adage about international connections that you want to try to do the connection domestically here in the U.S. if possible for IRROPS reasons, but I can't see how that would matter here.

-Because I don't have any set plans or anticipated travel timeframes, I'm not as concerned about specific fare differentials between say the IAD-SAT n/s and connecting itineraries across the various airlines, as avoiding one or the other being particularly worse between DFW/IAH and coming from afar if I take DL for example.

The major problem you have with DCA, is the perimeter rule, that prohibits most flights to AUS or SAT. Both DFW and IAH fall within the perimeter range. I'm not aware of any exceptions for these airports (I know of some for PHX, LAX, and SAN).

Otherwise, I don't think it really matters if you fly to DFW/IAH and connect from there to SAT, or fly first to another hub, such as CLT or ATL. Generally when I visit family in PA, I'll just take the AUS-PHL nonstop, but I have done AUS-CLT-ABE and AUS-CLT-AVP to get closer.

If it isn't too difficult for you to get to IAD, I'd just fly nonstop IAD-SAT. Less chance of weather along the way.

Agreed re: IAD (and I want to be clear that I'm not SUPER committed to the whole "DCA or bust, no way I'm going from IAD" crowd -- if the price/schedule works, so be it). Since it's all theoretical, again I can't speak to market dynamics as far as how usual pricing trends go. I was really just curious if people with experience flying this kind of route (yours being similar) have noticed that the intra-TX connections tend to work better, or if it's purely comfort/preference of breaking it up into chunks rather than one long leg and a short hop.

Know this route well as I live SAT and worked a DC job for years. IAD-SAT is your best UA option if you value direct flights/shortest duration of flight. (Add in the time required to get to IAD and the hassle of negotiating the TSA and gate access process versus the ease of getting to and accessing gates at DCA) Right now there's only one direct nonstop flight per day leaving IAD 7PM and arriving SAT 9:39PM on an Embraer 175. Originating from DCA requires a connection (usually IAH) but it's a pretty easy connection and even if you have to contend with a delay on the DCA-IAH leg there are plenty of IAH-SAT flights most days.

My preference would be to take a midday DCA departure connecting in IAH. Many of the DCA-IAH flights are also serviced by "Barbie jets" but they tend to be the Embraer 175s which are actually pretty comfortable.

Thank you for chiming in, that is precisely the use case I was hoping to hear about! Even though I'm more UA loyal than AA (or WN), I guess I always have this null hypothesis of AA via DFW for intra-TX traffic, so to the extent I was "looking for" this answer, it was to make sure that the UA via IAH option is "not terrible" or better, and not a situation where anyone with a choice takes AA for TX flying (WN too).

To the above, if the IAD n/s works, that is of course always going to the simplest, but as with a good number of DCA p2p flights, the late evening timing means that if plans dictate getting their earlier, you might as well hop a connection instead of waiting around all day. Slight negative preference against the IAD option merely for that timing aspect, and the logistics of getting there either during the afternoon westbound Beltway rush hour (coming from MoCo), or waiting around several hours at IAD (and actually then probably getting into the peak afternoon IAD departure rush through security and all that)....which to me usually mitigates in favor of the connecting option from the more convenient airport. Even when both options leave from DCA, I typically gravitate toward a connection at some point during the day rather than waiting around until evening to depart, unless my schedule dictates that.

The nice thing is that basically any trip I can foresee making will the leisure enough that we should have full flexibility of playing with all the options.