Its amazing people were getting so much money for homes back then with no skin in the game. 

If so, and you are in second position, if the buyer defaults on the primary mortgage and the lender forecloses, your second position will be wiped out and you will be left with nothing.The fact that the buyer has no actual skin in this game at all, because you are financing the downpayment, seems risky to me.  

My long term tenant (almost 3 years) has informed me that he’s having some financial issues. Last month the rent was paid in full, but split into 2 payments...this month he shorted me $250. I’m assuming/hoping he wil...

What makes it more difficult is that most of the 2-3 units that have been sold in the area have the potential of being converted into single family homes that can sell at about 1million, or can be duplexed down or up to attract a buyer looking for more luxurious units.  

No skin off my ....I have both so was sharing my experiences.

I have difficulty understanding any landlord that believes rent increase result in tenants moving.

The only difficulty is convincing the seller usually until you point out the perks to them as well.

How difficult is it to find tenants almost immediately after making my purchase and moving in?

The difficulty How did you find this deal and how did you negotiate it?

They have more skin in the game then you do.Make sure you get clear title.