There's < 2 months of seasoning for the purchase, cash into the deal is ~$975k w/o rehab (minimal planned so far - turnkey), purchased the property for 35-40% below assessed value, 825+ FICO, and would optimally like to pull out $975K-$1.15M of equity.Main scenarios we've thought of to accomplish this are: 1) structure sale of property from SMLLC to self and secure 30-year new purchase financing on deal (unsure if legal and tax implications if above initial cost basis)2) delayed financing (LTV restrictions a concern)3) cash out refi (seasoning concerns)4) DSCR (seasoning and rate competitiveness concerns)5) one of the above plus a HELOC, personal loan, etc.?

Downside on FHA is the Self Sufficiency rule where all units, taken at 75% of gross rents must at least equal the total mortgage payment including property tax, home  insurance and FHA monthly mortgage insurance.

High real estate taxes and older homes requiring a lot of repair and maintenance. 

I live in southern Ontario in Canada, and here if a tenant doesnt pay the water bill it goes onto the landlords taxes.

Then, move into Show Low STR for two years and Sell for up to $250,000 Tax-free.

You live in it for 2 out of 5 years and Sell for up to $250,000 Tax-free.

A 1031 exchange can be a great tool, but it’s typically used to defer capital gains taxes when you’re selling one investment property to buy another.

Will title insurance still cover any leans/unpaid taxes if any? 

Pretty rare from what I see that cities allow or want this....turns single family neighborhood into multi family and most of the zoning people don't like this.Plenty of issues from their point of few of why they don't like it.....parking is one...now no one parking in garage, and potential for more cars...so now 3-4-5 cars in the street.More taxing on the water/sewer/trash/police/fire/city services.I wish you the best of luck with this. 

We run the number of these properties on the calc of BP and they would give us with conservative numbers on the rehab (estimating to put more than needed) and on the rents (market rent but conservative), good returns, like Cash on Cash return (CoC) between 2-6% and Cash Flow between 986 to 12000 per year, so anything from 100 month to 1000 a month, after expenses were taken, so from this cash flows only taxes are missing to be taken, with some properties needing us to put from minimum 40k to 90k down including rehabbing them.