In your experience as someone who understands real estate analysis at much greater depth than I do, what are the main factors to look into?

@Jonathan Ghione S8 tenants are getting more and more "spoiled" in our area - Metro Detroit.Too many newbies and Turnkey companies are waiving application fees and security deposits, also giving them recently rehabbed, really nice homes.Then they trash them.Have you stopped and thought about WHY someone qualifies for a S8 voucher?

City of DHS is tough right now, they are enacting new very strict STR rules and it's tough to manage the process and fees unfortunately. 

We are not tied to a particular coastal market, since we understand that certain areas have higher taxes/fees/regulations/hostility to STR/flood insurance/etc. 

Then your system development charges along with all the other fees for building permits..

.- Explore strategies like 1031 exchanges to defer capital gains taxes.Deductions and Expenses- Know eligible deductions: mortgage interest, property taxes, insurance, maintenance, and management fees.- Maintain detailed records of all real estate-related expenses.- Use cost segregation studies to expedite depreciation of your properties to offset large income gains.Entity Structure- Choose appropriate legal structure (LLC, partnership, or S corporation) with consideration for different tax implications.Tax Credits- Explore available credits, like energy-efficient or historic rehabilitation credits.Qualified Business Income (QBI) Deduction- Check eligibility for QBI deduction, providing up to a 20% deduction on qualified business income.Record Keeping- Keep accurate and organized records for tax compliance and audits.State and Local Taxes- Consider varying state and local tax implications, including property and income tax rates.Tax Planning- Engage in proactive tax planning, consulting with professionals for a comprehensive strategy.Tax Changes- Stay informed about changes in federal, state, and local tax laws affecting real estate investments.Remember to consult a real estate tax professional for personalized advice based on your specific situation.

do you mean leasehold rather than fee simple ownership ?

You will usually get mailers from attorneys that do this yearly they will take a fee based on your savings. 

And then write up a lease that says month 1 & 2 rent is $X (market rent plus hassle factor.).

I have not factored in depreciation yet.Am I thinking about this correctly?