Finding an investor-friendly agent is key and they should be able to help you with 1-4, I'd say talking about those questions you asked would be the perfect thing to ask any potential agents you interview! 

Hello Friends,I own a 1982-built ground-level condo (one unit above, one below).

In my market, which is a fairly economical place to build, I am friends with full time builders that are in their properties about $150k/door for construction level finishes.  

I’ve considered multifamily or duplexes, but from what I’ve heard, they’re unideal right now, so I’m leaning towards STRs.I’ve put together a list of areas that seem STR-friendly with good tourism appeal, and I’d love to get feedback from people who know the San Antonio market well.

A friend of mine had a similar journey - they turned their old home into a rental property and soon realized they loved managing tenants and exploring ways to add value.

Hey Christine, I might be biased, but you could look into Cleveland, Oh.Here are a few things to consider against investing there:- Slower appreciation compared to some other markets- Harsh winters, which can lead to higher maintenance costs- Many discounted single and duplex might need repairs or updates, especially if the previous owners haven’t kept up with maintenance over the years- Some local regulations to be aware of (nothing crazy, but worth noting when trying to close deals).But there are also some solid reasons to invest in Cleveland:- Affordable properties in the $100K-$300K range- Strong long term rental market due to a high rent to price ratio- Landlord friendly laws overall- Potential for great cash flow- Opportunities for Section 8 tenants- stable market once you have the right team in placeEvery market has pros and cons so it comes down to your budget, risk tolerance, and finding a reliable crew you can trust.

Do you build it with the intention of renting it or just for family/friend use?

You should look for an "investor-friendly" PM company that knows how it is just dipping your toe into the water of buying a home/condo/townhome.. 

Here is what we have found and I will probably catch some heat for some of the things I have to say, because it does not sound "investor-friendly".

It's a smaller, family-friendly community that draws a ton of repeat vacationers (families will book the same place year after year).