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

@Richard NguyenHere are some of the downsides of putting real estate into a self directed IRA or 401k.No tax deductions: You can’t claim deductions for property taxes, mortgage interest, depreciation, repairs, improvements and other property-related expenses.Property expenses: All expenses, repairs, and maintenance costs must be paid with IRA or 401k funds, and you must pay others to do repairs and manage the property.

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

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.

@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.

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.

My prediction that these "bans" and regulations are all going to pretty much converge into reasonable middle ground regulations (mostly including taxes fees) is still looking very good. 

Is your DSCR ratio greater than 1-meaning are you cash flowing (according to the lender's criteria of mortgage, property taxes and insurance (and HOA) if applicable).

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.

Knowing this information will help you identify the right professionals to bring on board.At minimum, your team team should include:Financial Advisor: to help with investment strategies - portfolio diversification and risk management.Real Estate Agent/Broker: to help with property acquisition and market analysis.Accountant or Tax Advisor: to help manage financial records, tax planning, and optimization.Attorney: to provide legal counsel for contracts, agreements, and investment structures.Mentor or Coach: to offer guidance, insights, and industry knowledge.Networking and Relationship Builder (for everything else you will need): to connect you with potential partners and collaborators.