Something to dive deeper with a financial/loan professional.

That could be market knowledge, ability to rehab a property - something that can give you an edge over other experienced RE professionals in the market and asset class you are working in. 

I was able to become financially independent in 2 years with two properties.

If you need financial help, ask under the "Finance, Tax, and Legal" forum.

Thankyou @Paul Azad, the relationship between Monday and RSN was described as a joint venture, meaning both groups would be responsible, and actively involved, in asset management and decision making.  

(Due to some financial issues with him in the past, I'm not willing to cosign for him)  Would a rental agreement with the roommates suffice? 

With a passion for finding undervalued properties and transforming them into profitable assets, they are eager to learn, grow, and build a successful real estate portfolio.

Without having much info, I would need to know the financial situation of the 'close family' to determine a best approach.

Do you have the financial strength to hold/carry these lots if they don't sell quickly? 

Regular tenants may have more of a support system when they have bad financial luck.