Also, what about internet, trash and security?

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

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.

The short version is this:  If you're willing to pay (considerably) more for the security of guaranteed rent, they are probably worth hiring.

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.

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

Think of all the things that could go wrong and see if the lease addresses them: unauthorized pets or tenants, early termination, security deposit, lease violations, late rent, eviction, lawn maintenance, parking, etc.5.

To supplement my down payment, I have secured $50k via gift and inheritance.

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.

Security Deposits / Escrow: If you would like to use Baselane for an escrow account, you can simply open another sub account that is separate from your day-to-day activities.