You could purchase the first one through conventional financing in order to give him a chunk of change up front, plus put some skin in the game.

Most lender do want you to have some skin in the game, typically 10% minimum. 

I am not a newbie; I have skin in the game, as I am house hacking.

As for hard money lenders, they typically require you to have skin in the game, especially when it’s your first investment.

The floors were extremely unleveled and the new flooring was already coming apart, in one unit a previous landlord spray textured over every surface of the property including the thermostat/door knobs/trim, in both units the kitchen and bathrooms were falling apart and barely above usable condition, the staircase in one unit was obviously illegal it was so steep, and the walls/ceilings in both units were a mixture of poorly cobbled together panels, cracked lathe & plaster, suspended ceilings that should have been replaced a decade ago, and entire surfaces made from something I couldn't determine.  

They want the "skin in the game".Another note, the numbers you used in your scenario are almost the exact same numbers for the past purchase + rehab I did. 

Banks make you keep some skin in the game even if you can take all the money invested in the property out. 

You are in better position than most since you can put some skin in the game.

We skim coated the basement walls because they were textured.

It is textured.