You may want to pay an appraiser to determine the value at the time of inheritence.

That said, even with conservative rental income estimates, my living expenses would eventually drop to several hundred dollars less than what I’m currently paying in rent once the house hack starts generating income.I do have cash reserves to weather some rough patches, but the idea of pushing my budget this hard makes me uneasy.

Now if I pass that income as management fees to S-corp, I pay $3.5K (SE tax) + $800 (LLC fee) + $1700 (CPA + bookkeeping) = $6K in total.

Grow wide first, then deep (pay off)- your little expenses add up fast

Has anybody dealt with Investors Edge and gotten 100% financing after paying $3995 membership fee?

This would likely take coordination with a tenant at some point - (ie - plenty of notice to them that they must vacate in order for you to sell the property)Since your current home is free and clear -  you could do a cash out refi or take out a new mortgage on the new house to be able to buy your paren't house and pay off the mortgage.  

Regarding your other questions:  - If the going value is $260/SF, why would you pay more than that?  

Homebuyers will always pay more than a REIT type investor.  

Being out three months of rent plus $1,500, I'd be better off handing back their SD and forgiving the month of rent they couldn't pay.  

if he performs a service for you, just pay him for it.