My trouble is I don't know how to start the ball rolling.

First time poster, long time listener/reader-So, I'm trying to get our real estate portfolio rolling.

The lender reached out and as part of their “loyalty” program, I can refinance again, no fees upfront or rolled into the loan.

I figure I'm going to make some mistakes, so having conservative estimates will give me the cushion to roll with the punches.  

I rolled my 401k into a self directed IRA- no penalty and purchased a house with the funds!

One is cutting and back rolling, the other is rolling. 

However, they may or may not be able to use the entire rent roll as income.

You will need most likely a minimum of $1,100/unit (assuming the $3,315 rent roll is for all 4 units) to even begin looking at this as potential for a rental.Because you are still missing some factors, it will only hurt the bottom line.

Maybe since you are young you can househack and build up your savings and roll the equity into other projects.

They should roll into your personal return on your schedule E.