Trying to get myself out there but I know this is a really special community to be a part of.

From the little I know of San Antonio (I am a wholesaler who specializing in selling STRs nationwide) its not a super hot Airbnb market but the amount you expect for rent sounds pretty conservative. 

It seems like every city, county, and state has its own rules, permits, and tax requirements for short-term rentals, and I’m finding it overwhelming to navigate all the different layers of compliance.For example, some places require business licenses, transient occupancy tax permits, or even special zoning approvals.

A good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.

If you didn't find a property manager yet, my company specializes in multifamily properties in the greater Phoenix area and are taking on new clients.

Starting with local credit unions is a good idea.2 - I recommend starting your search with a Realtor who specializes in working with investors.

I didn't read the website you were referring to earlier, but I know that there are attorneys who specialize only in dog bite cases - because there are laws on the books that give specific penalties that are non-negotiable, related to dog bites.  

Generally it's a mix between (a) spec builders, the type who specialize in doing in-fill lot's (b) investors, as it is a normalized flip strategy (c) owner occupants, especially in high desire neighborhoods, who are a-ok with taking on the project and even some are excited that they get to build a new home in often old neighborhoods. 

Most value adds involve work   Some require specialized knowledge.Here is a list of why adding ADUs in my CA market is typically a poor RE investment:1) The value added by the ADU addition is often significantly less than the cost of adding the ADU.

I know a friend who is an attorney, although they don’t specialize in housing law.