@Ben Cochran I hope you have factored STR tax savings into your cashflow and ROI as it can be significant.Leveraging equity to purchase a short-term rental (STR) in Tampa Bay can diversify your portfolio and potentially generate strong cash flow, but it also increases your financial risk.While your properties hold significant equity, adding debt from HELOCs or a DSCR loan could strain your finances if STR performance fluctuates or costs rise.

Truthfully, I don't think a Capitalization Rate of 8% is terrible plus you'll have an appreciating asset along with the tax benefits.  

What are some pros that I can highlight from the seller’s perspective.Here are a few that I’ve come up with:1) monthly income at a higher interest rate;2) avoiding a larger tax bill by reducing the purchase price (on paper);3) a promissory note that they could potentially sell down the road.Any other major ones I am missing?

Here are the numbers:Purchase price: 300k @5.5% (might be able to negotiate new exterior paint job credit)Monthly costs: mortgage- 1703 tax-245 (2933/yr) insurance- 167Market rents are 1600$ easy for both sides as is but currently being rented at 1410 and 1325 tenets pay all utilities (separately metered)Planning on putting aside 20% of rents for Maint, vacancy, capex and will be self managing property.

Finally, we do not care about your tax returns, etc.- since these loans are primarily based off of the asset as collateral.

There is much confusion about the 4% and 6% in property taxes.Non owner occupied property is taxed at 6% of the value to get the taxable value.This does NOT mean your actual property tax is 6% of the purchase price for rental property,In reality property taxes are about 2% of the purchase price for rental properties and about 1% of the purchase price for owner occupied properties.Google Greenville County Property Tax estimator and play with it and get a sense of how it works.3.

My go to for lowest hassles, taxes and  transaction costs are Lease Options or selling directly to the renters. 

Thanks Tom Wheelwright for writing the book "Tax Free Wealth". 

The company making the offering must take reasonable steps to verify that an investor is accredited, which may include checking financial statements, tax returns, or receiving confirmation from a broker-dealer, attorney, or certified public accountant.These regulations reflect a balance between making capital more accessible for businesses and protecting investors from risks associated with unregistered securities.

Use a promissory note drafted by an attorney to outline loan terms, including an interest rate that aligns with IRS Applicable Federal Rates to avoid gift tax issues.