People, lease option the joint!

The lease has joint and several liability and is auto-renewing and we'd like to keep the lease's end/annual renewal date at May 31 (new tenant is moving in Aug 1).

It's up to you if you want to risk the a** ache of small claims court or just pay the $800 so he'll shut up and you never have to see him again.

Also if its a Joint loan you can technically buy up to 7 units. 

Joint ventures are a wonderful thing.

@Jeshua J Snyder - and if you need partnership and JV advice:PARTNERSHIPS / PARTNERINGHow to Effectively Conduct Joint Venture Agreements as a Real Estate Investorhttps://www.biggerpockets.com/...

@Miguel Vasquez I work for a rent payment service and one option we recommend for tenants without a bank account is a prepaid debit card that allow ACH debits, such as the NetSpend card.  

It looks like options 1 and 3 should be correct based on the info provided...if you have a "joint and several liability" clause, then option 2 would come into play.

Me and my husband are hoping to make about 135K per year from rentals.Lets say, for simplicity, that 35K goes on expenses, mortgage interests, property taxes, etc and I am left with 100K income from rentals (In your example it was 100K income from W2 and rentals, but in my example its 100K only from rentals)So, do I understand correctly (and this is a copy from your post above):Since I am married and  filing jointly.

Reposition the shingles that are still good, weave in the new/replacement shingles... know where and how to nail them in, properly of course (laying them in correclty, no double overlap and all the tabs lining up as they should); nail down the adjoining ones too; seal all the worked shingle joints in that area; get up on and check the rest of the roof of course to make sure no other damage it present...Oh, but it'll probably only be about 10 shingles, but you'll need 1 whole bundle to get those 10-12.