Hey @Connor O'Brien - There is a list that CHA releases each year that states the maximum rent they will pay in certain chicago areas based on bed and bath counts. 

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So a lot of little guys like me are paying double for their money.

My mortgage increased earlier this year as my home owners insurance went up due to the company closing and my escrow didn’t have enough to make up the difference so I’m kind of pay check to pay check right now.

In the future you could add in penalties for being late and possibly a bonus for being early.

How would you pay for that?

I was thinking I could put down the 50k so he had enough to pay off the heloc and make payments to him for the remainder to be paid off in 10 years with new renters.

We have users who have been paying the same price as it was 4 years ago when they originally subscribed.

So you are already paying tax on the income.LLC taxed as an S Corp would be different, but I doubt that is your case.

By paying off the land loan through the new construction, it removes that lien and allows the construction loan to move into 1st position.