I would urge great caution when choosing neighborhoods and even blocks to invest in as things can go uphill or downhill very quickly.

What is the most pain free (and, ideally, tax-free) way to accomplish this?

Maybe something happens on the block which pushes rental rates down, but still provides a sale option.

There was a road that led to it, but the neighbor that owned the land that the road crossed had piled up a huge pile of debris to block access. 

That said, they've gone through some huge growth over the last couple years and maybe they're having some growing pains? 

As someone in the game for more than 30 years, there are cities I have always been interested in, but have no interest in a one-off for myself so this is a great opportunity to get exposure in a market without any of the operational pain.4.

Think of potential pain points or ongoing vendor tasks that you can keep an eye on remotely with cameras in addition to security.

After reviewing the latest ordinances, reports, and city guidelines, here’s a summary of my findings as of 11/18/2024:Key FindingsPermit Types and Fees:Type 1 (Owner-Occupied): $300 for 3 years.Type 2 (Non-Owner-Occupied): $450 for 3 years.Density caps apply to Type 2 permits (12.5% of block face).Enforcement:3 violations in 3 years lead to permit revocation.Fines up to $500/day for violations.Hotel Occupancy Tax (HOT):City: 9%, County: 1.75%, State: 6%.Platforms like Airbnb and VRBO will remit directly to the city starting Feb 2025.Platform Obligations:STRs must have valid permits; unpermitted properties will be removed by platforms like Airbnb.Special Exceptions for Density Limits:Require approval by the Board of Adjustment (BOA).Zip Code BreakdownI focused on these 11 zip codes:Under San Antonio Rules:78205, 78204, 78215, 78210, 78212, 78245, 78258Independent Municipalities (Separate Rules):Alamo Heights (78209)Leon Valley (78238)Helotes (78023)Next Steps:Research density caps and zoning in specific zip codes.Dive into independent municipality rules for Alamo Heights, Leon Valley, and Helotes.Evaluate market maturity and income potential using tools like AirDNA.If anyone has experience operating STRs in San Antonio or these specific zip codes, I’d love to hear your insights, especially about density limits, enforcement trends, or community sentiment.Thanks in advance!

The unit we have, one block further back from the beach we have been getting a little over 35k gross per year.

No biggie my bank sent me the fraud alert and I had them block the charge.