Once you have income hitting your taxes you can refinance and move there.4.

Accounting System with "Control" ChecksSoftware to manage revenues, expenses, payroll, and taxes, etc., and ability to verify receipts and transactions (the verification is done by upper management to check and validate the revenues and expenses)4.

This is helpful for monthly bookkeeping and tax return preparation. 

Land Entitlement is one of the riskiest Real Estate investments for several reasons:1) High Upfront Costs with No Guarantees: We spend tens of thousands of dollars on due diligence to ensure the property is suitable for development.

@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.

(They both shrink your pool or buyers and combining them really shrinks the pool.)Assuming you don’t plan to do a 1031 exchange you’ll also pay higher taxes if you can’t spread them over two calendar years, but not much. 

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.