I have a unique situation.

-All in price: $250k-ARV: $400k (conservative) -Rent price: $2500/mo-6 month cash out refinance: $400k for 75% LTV, repay investor $300k (20% over 6 months) -Mortgage after refinancing: ~$1400/mo (30 years at 4%)Cashflow numbers:Rent: $2500Mortgage: $1400 (64%)PM: $300Maintenance: $500Remaining: $300/mo cash flow, with $0 left in the deal by myself and the investorWorries, Issues, and Concerns:*Occupant must let myself, my realtor, and contractor/inspector walk through the house prior to purchase*based on the condition of the house, (kitchen or floors don't need to be redone) then the price point of the sale can be raised up to $250k all in*Possibilty of not being able to refinance.

Often properties that are unique like this are difficult to value with comps so where did you come up with the $700k figure.

The VA Loan is an incredibly powerful tool, so read up on it and talk with folks (like me) who have leveraged it.Let me add in a note of caution, because you are in a unique situation as a cadet.Be hyper-cautious about fraternization. 

Slightly fancier interior doors and a painted/unique front door.

See if you can find a lender who would be willing to use the same appraisal I have seen appraisals challenged before but it usually due to the property being unique and there being no real comps in the immediate area. 

It's a unique and challenging market we live in!

Safe may mean using low rate fixed loans on bread and butter houses, cash for unique opportunities.   

We have been investing a ton of sweat equity and giving it a very unique custom look and feel What was the outcome?

@Pandu ChimataAgree with @Natalie Kolodij that you should make sure your tax professional is comfortable with STRs.STRs have unique treatment under the passive activity loss rules and unique treatment regarding depreciation...They should also not be reported on Schedule C unless substantial "hotel-like" services are rendered, as noted above.