He advocates buying on the MLS at full price (he says he can "over pay" and then he can use "gator lenders" to cover the down payment, closing costs and he has no skin in the game.

Is he going through a financial difficulty and that is why he is late with the payment?

You have skin in the game in the form of your entire net worth.

Where's the skin in the game like I had to do? 

I'm not a buyer in the city proper, but you shouldn't have difficulty selling it.  

Not that I'm aware of....you need skin in the game.

Many people are suggesting to do a 1031 but have no idea what your gain / tax is(if any).Co-ops in the tri-state area 'normally' don't appreciate a crazy amount.The main reasons is the high monthly maintenance costs, over-leverage of the board, potential difficulty of buyers getting a mortgage and the approval process of the buyer.With that said, talk to your CPA to discuss what your gain / tax would be before thinking about a 1031 exchange.If your tax burden is low, don't bother with the 1031It may be possible that you have suspended passive losses to cover your tax burden.best of luck.

Or am I overthinking the difficulty of managing these properties, is a property manager necessary?

This change makes it harder to use large deposits as a protective measure, which might explain part of the difficulty landlords are facing in managing tenant risk.As for the post-COVID surge in applicants with problematic rental histories, many landlords across Baltimore have noted similar patterns.

Really cool way to do it so all parties have some skin in the game.