Should I send him a letter now saying that he has the right to an initial move-out inspection so landlord and tenant can be present so landlord can point out what he needs to repair for he to get more of his security deposit back?

Negotiated down about $5k from initial offer.

I know this is VERY broad and specific numbers would need to be analyzed, but I'm merely interested in ppl's initial thoughts on the issue.

This was my first foray into the real estate market.I think I was a little too optimistic with this house, it’s old, I had gotten it down from initial asking of $280.

Its the 4th now and he hasn't paid or responded to my initial text on the 1st asking if he received it, or my follow up text yesterday. 

In my state of New Hampshire they have ruled we ARE allowed to file evictions and I started one with the help of a more experienced associate about a week and a half ago and the initial paperwork put the living fear into my tenant and he paid what was owed and we made arrangements for this month.

But from my initial DD, their estimates of repair costs and comps used seem to have wild ranges.

Not so fast....the first thing I wanted to do was to get all of the appropriate documentation (T-12, leases, contract services, rent roll, etc.) to make sure all of the initial financials that the seller gave us were correct.

My initial plan, is to target distressed listings on sites like Zillow/Redfin, to start.

Another aspect that made the deal interesting was that it came with an extra lot, which I can parcel off at any time and recover the whole initial downpayment.