I’m a little concerned about off season rentals.

You should have all the contracts readily at your disposal. having been an agent for 2 years already, it's really concerning that you wouldn't readily know the contracts for such as of yet, so I have to assume you have done exceptionally little the last 2 years. 

Why even concern yourself with the legality if it’s self serving and harmful to your family member?  

Since the house is for sale, the most important concern is marketability.

My opinion, that most of these marketing company produces programs, whether we want to call then educational, mentorship, counsel, advice or whatever are CRAP, and possibly dangerous, is based on my experience, knowledge, and observation over a 45 + years real estate investing career. 

Would a low enough sales price make all of my concerns go away?

There are some concerns around taxes and insurance to be mindful of, but the job market in major Texas cities is unreal.

My concern was that it was too far from the heart of San Antonio.

The contract with the wholesaler also expires on Monday the 27th, so I have my concerns about this just being a stall tactic to get out of the contract.

At this point, I'm not so concerned about achieving that exactly, but if my REI journey takes me there on my way to (or even after) financial freedom, then I'm all for it.There's still some work to do to prepare financially for "the first deal" and that moment legitimately appears to be about 2 years away.