@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.

This is helpful for monthly bookkeeping and tax return preparation. 

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?

Without seeing your lease, if the lease says that 'charges are due as additional rent' the charges may fall into housing delinquency law.

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.

Obviously, the rules will differ from state to state.The most successful buyers have trusted bidders with cashier’s checks in multiple denominations (for cash sales) and the actual buyers have field runners and people to monitor multiple prospective properties at a given time and check sales status for postponements due to BK, etc.This is the case in larger metro markets where many properties could go to sale but few do so.There are often better ways to acquire properties then auctions.

Don't take their unofficial advice as gospel, so do appropriate due diligence prior to making changes to the 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.