On thing to keep in mind are potentially elevated maintenance and landscaping costs, as the weather an be extreme ranging from intense rain to snow flurries on the beach. 

I also added 4 new basement windows that provide proper egress, rewired the basement and landscaped the yard. 

Every year my mom tells me how high her home owners insurance is and it goes up every year.Having lived through Hugo, I am nervous about buying anything ocean front, seeing so much wash way must have left an impression on my young mind.Definitely agree with you about having a good realtor to navigate the landscape.

You should not have to do anythingThe onsite manager shows and rents apartments, oversees third party vendors like, maintenance, landscaper, pest control, pool.

A few benefits of a Townhouse vs a SFH is that most Townhomes will be less expensive, and a lot of their HOAs cover the exterior and font landscaping of the home.

For primary residence #3, we bought in the path of progress; so, not a live in flip per se but similar in that we will get high organic appreciation and also add value through easy rehab such as refinishing floors and railings, replacing fixtures, improving landscaping, upgrading tile, etc.

Follow what is going on in the local landscape as far as laws are concerned. 

I'm not new in this space and know how to build long-lasting relationships over many years.Is there something I'm missing about the dynamics of hiring smaller contractors (handyman, landscaping, etc) in San Antonio? 

Do a flip that is just paint, landscaping, flooring, reroof, etc.  

Will mean a less competitive landscape for landlords that do consult attorney's and follow the provisions.