I find myself trying to be easygoing to avoid ruining the relationship and turning a good tenant bad. 

EDUCATE YOURSELF - yes, it will take time, but will lead to a selection that better meets your expectations & avoids potentially costly surprises!

Money may be tight and you could avoid a vacancy for a few months.

What you want to avoid is having your coverage dropped.

I'm trying to avoid backing myself into a corner here. 

Generally, I would avoid trying to "time" the market.

Why not just partner with him and avoid the 2 closing costs?

EDUCATE YOURSELF - yes, it will take time, but will lead to a selection that better meets your expectations & avoids potentially costly surprises!

Any wholesaler worth their salt is taught to avoid you guys like the plague. 

If you intend to have the cars towed, calling him and telling him this a week or so ahead of time would give him some time to move them.That way you avoid (as much as possible) making an enemy both with online reviews and in person.Just my 2 cents.