If that person want profit from each deal going along, you can make agreement with each deal you are doing. 

You must deposit to a trust account at a Mass bank.

I checked with my bank and was told that yes, I can deposit postdated checks.

Only the person running the club chooses potential investments.

That would help as it would be seen as an income property and some banks are willing to lend on that.

I do have some personal debt that I'm working to get rid of.

I personally have lived in both..

No, you are looking for a CRE (commercial real estate), bank or SBA loan on this, "DSCR Lenders" are for 1-10 unit residential properties and typically don't allow any senior care or tenancy like that

I did a podcast episode on this strategy about a year ago called “Creating Your Own Downpayment Bank”

I personally have no problem driving in the rain if there was any.