I’d reinforce what an eviction on his record will do to his ability to get subsequent rentals with all the background checks going on today.  

This means that the cost of this loan is reduced per use with every subsequent use of the same money. 

I’d recommend using your spouses for the second purchase so that, if not exempt, your VA funding fees will only be 2.15% for first-time use each time instead of bumping up to 3.3% for subsequent uses. 

You will pay an increased funding fee due to the subsequent VA loan, but you still don't pay a down payment, etc.....Although I am pretty savy, I am still not an expert so do all your research etc.. 

I think some of the siding may have also been damaged by snow or ice sliding down the others roof and probably into the side of my building.

I'd give him the legal notice, and return his deposit (yes, it will be painful, but if you don't have proof, IMO it's a lost cause, not worth the hassle/stress) , and offer him a sliding scale, $400 if he moves out next week, $300 if he moves out in 2 weeks, $200 if 3 weeks, contingent that he cleans up the place too.  

I wouldn't pay for an actual inspection until you have it under contract but you can offer to slide someone a few dollars if they will come out and do a walk through with you.

Hello Jay,it copies and paste a little backward.. but by my sending this in and subsequent meetings with the state of Oregon investigators its clear that assigning contracts with no intention to buy IE its your business model and advertising in ANY manner a property you don't own is simply illegal in this state.. 

And the caps on a cottage style roof, and not sliding off with a 18' drop.

What that means is that normally once your holding period has passed a year all the gain from that property or subsequent properties is generally treated as capital gain.