He'll see me soon enough, he can get it then...All this peer pressure reminds me of something....can't figure out what.  

Many property managers send out reminder notices of impending deadline a month in advance, small landlords might give a courtesy call directly to their tenants, but either way start showing the places right after that date so you don't risk going without a tenant and they understand you are serious.  

Having taken massive action wholesaling in the last two months I'm reminded of the flywheel principle.

This really reminds me of the buy here pay here car lots.

If the unit is in a good condition, keep showing the unit.Keep in touch with him to make sure he moves out in time AND remind him to keep it in a good condition or clean up.

I've constantly reiterated that they should keep me posted or else a late penalty will be assessed but for the most part have been lenientThis month comes around and I reminded them as I usually have to and mentioned that if they don't pay within a day (rent is already 4 days late past the grace period)Tenant proceeds to blaming the late rent on issues and it looks out of frustration they issue a 60 day noticeAdvice requestedAssuming they're moving out in 60-days, how do I get rent for this and the successive months until that time?

That reminds me--you should have a decent idea of who the other LP's are as you'll be in bed with them and they may need to write checks.  

A reminder of the tax benefits of the first two is appropriate as well, if the letter is informal enough.

Your situation reminds me of one of my properties- one I fell in love with due to its old architectural bones and the thought of possibly living there. 

Read your goals regularly to remind you of what you ought to do.