The estimate rehab budget was $133K and I gave him roughly $30K to start for various deposits (Roofer, Windows, Framing, Etc).

The lease termination fee needs to be paid at the time they request this, do not substitute the security deposit for this purpose.This will ensure compensation for time, money and effort needed for a tenant turnover, including advertising and showing costs, regular repairs, utilities during vacancy etc.

I can always make deposits/contributions into the SDIRA though.

The vast majority of lawsuits against Landlords are for wrongful eviction, security deposit disputes, and Fair Housing Violations.

The “tales” of nothing down/seller subordinates “down payment” done successfully almost always hide the most important information - that the buyer either provided additional collateral (such as real property owned “free and clear”, a certificate of deposit in an amount greater than the down payment required, or the buyer is financially strong enough that part of the financing was in effect a personal loan or line of credit. 

I have heard mixed responses on whether to charge both first and last month’s rent and a security deposit, or just first or last month’s rent and security deposit.

They've been fabulous from the very beginning, responsive, polite, paid their first month's rent and deposit early, etc.

My tenant of 1 year just moved out recently (work transfer), but during the move-out inspection we found that one of the 10X10 bedroom has all four side of the wall covered in screw holes from the time they used it as a computer room (I believe the holes were from the sound deadening foam that they used to attach to the wall) So I was wondering what would seem to be a fairly reasonable cost to be deducted from their Security Deposit for the excessive holes and needing to repaint.

We don’t bother with security deposits, so there’s no recourse against the outgoing tenant who destroyed the furniture that was ‘new’ (meaning great condition off of Craigslist) just a year prior.

The vast majority of lawsuits against Landlords are for wrongful eviction, security deposit disputes, and Fair Housing Violations.