There were some carryback rules in the past but not under the current tax regime.

Listings with higher engagement and satisfaction may be prioritized in search rankings.

We have our Guide Book on the counter in the kitchen.People like to have something to look through, plus other guests leave flyers from places where they ate etc. with notes like, "Great food" etc. written on them. 

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!

I have enough cash in the bank to purchase a small  2bd, 1ba SFR (already cash flowing/w tenant) outright.

What part of Philly is your duplex in? 

If so, the STR strategy could be beneficial in your case.

You don't eat an elephant in one bite.Focus on whats in front of you.

In my experience, you can purchase the existing home and the encroachment is grandfathered in, meaning the vacant lot owner can't force you to move it.

Vacancy is often around 5%, particularly in high-demand markets, though this can vary by location.