Yep, just document everything, and take pictures of everything you are deducting for.

Life if a repair isn't up to my standards, or he doesn't like taking directions from a woman.  

If they refuse, I would send an itemized bill for the month rent due, deduct the security deposit, and return any interest.

Standard loan 20% down...I plan to re-fi after one year and get my cash back.  

He is purchasing a house (SFR) for $270k with about $9-10k down, the seller is carrying a 2nd wrap/note (1st is standard mortgage #217k balance @ 5%, PITI $1690). 2nd will be about $300/month PI.

All it takes is one major issue, such as the insurance deductible for a storm damage claim, a tenant to do damage above and beyond the security deposit - never mind the loss of income while it's being repaired, or evicting a tenant who hasn't paid, etc. ... to turn break-even into a loss.

: Standard Rules of Thumb: 2% rule - you are at 1.15% (not bad or good, depends on other expenses) , 50% rule take 1150 - Principal Interest Payment only, to estimate whats left over Assuming you will be managing yourself once you move out.

In fact if you take a look at the standard forms for purchase and agreement for your state or any state that you want to do wholesaling in, you will find a numbered line that says Assignments/Assignability. 

whats good about conventional is once you hit a certain equity mark PMI goes away and it it a standard conventional mortgage, additionally you can purchase right away rather then wait 1 year assuming you are able to.

I know I cannot take tax deductions on a personal residence, but I am under the impression I can take deductions for the cost of a rehab on a rental property.