However, the actual deadline would be April 15, 2025 my individual tax payer filing deadline per Rev.

No, we are not perfect like any business, and we always welcome feedback as long as it's constructive and professional.

If an issue is professionally fixed where the buyer feels confident it was addressed COMPLETELY and CORRECTLY, then I think you don't need to worry so much about resale value.

You will truly be raising the clock, as each day will cost you very significant money.  12% interest on $250k is $2500/mo, or about $80 per day in interest, not including your other carrying costs (utilities, property taxes, insurance, HOA). 

Are the tax savings worth all the hassle of STR.

The biggest advantage of using someone local to where you're buying is that they will understand taxes, insurance, and similar items very well when it comes to DTI/DSCR calculations and payment quotes, and they will likely have a local network of service providers for ancillary services (survey, inspections, etc).

If you need financial help, ask under the "Finance, Tax, and Legal" forum.

Some numbers below for reference: I currently am taking home about 140,000 pre-tax.

Agree 100%, trust and transparency are what set professionals apart in this industry.

After he teamed up with a local intermediary in the Bay Area.. from what I read in the Wall Street Journal, Lockton has been helping investors streamline these moves.. he ended up freeing enough capital to invest in a mixed-use building in San Antonio that we’d been eyeing for a while.I’m no attorney or CPA, so I’m not giving legal or tax advice here, but there’s definitely something to be said for repositioning your insurance to fit your broader investment goals.