NCREIA sounds like a good idea.

Here are the projections for 2024 to give an idea of expected returns:2024 IncomeLong-term Income$8,400Gross STR Income$45,500 (based on AirDNA projections)Additional STR Income$5,915 (mostly cleaning fees)Total Projected Income$59,8152024 ExpensesSTR Expenses$16,453 (32% ratio)Mortgage$34,476Insurance$707CapEx$3,600Taxes$2,729Total Expenses$57,965Projected Cash Flow$1,850CoC Return2.79%2024 Additional ReturnsPrincipal Paydown$2,930Equity Appreciation$16,200Mortgage Interest Deduction$7,571Total$26,701Total Projected Returns$28,551Projected Return on Investment43.1%Projected Return on Equity21.4%The CoC numbers are not impressive, and the property only cash flows as an STR, which carries some risk.

Save as much money as you can from working to use for a down payment. 

The combination of these tools will give you a good idea on what you can expect.

Any other ideas to ensure rent payments?

Last thing I'd want to do is rush into a property, miss red flags, and end up getting in a bad situation.Is a rehab in a C class neighborhood (which is what it would likely be) a bad idea for my first property?

Was looking for some better ideas for tax planning, and saw this one, but then wondering now how much money I need bring to table.I also have another house I could sell, and maybe 1031 exchange with like 300k equity in it, so not sure if that would help.

That’s sounds like a good idea.

Its free to use and puts the idea of systematizing in your head.

It sounds like if you just structured it giving him commissions it would not really work out considering he clearly wants more involvement/skin in the game on the project.Maybe just split it LLC 50/50 and the commission savings is a preferred return over his split on the exit?