This would be both a risk mitigation strategy as well as a bite size learning opportunity as I intent to manage close to all aspects of these for at least the short term (want to be an expert in the day-to-day operations before hiring this work out). 

Of course, after you tell them that, you do keep trying to help them, and work out a deal that everyone is happy with in the end.

How would the tax computation work out on a 30 year note?

Build a portfolio of routine service call tasks and light remodels with actual costs that your Clients can compare to outside vendor's similar work.

I have had a couple of opportunities to market similar properties time on the market, desirability etc and having a sharp property with decent ceiling fans helps.I think it depends some on the property and the target audience as I have investors with lower priced multi-units with no fans on purpose that work out very well. 

@Jacob RossTwo answers for you- more times than not - equal partnerships don’t work out nearly as well as going it alone.  

Going the DSCR route will also not work since he will be subject to a PPP at the time of refinancing into a primary loan.Putting a tenant there for a year and then anticipating to move in after a year may not also work out depending on the states Laws regarding this. 

Im a Realtor too so I just pulled in the driveway and talked directly to the owner and it took a few months but I was able to keep in contact and work out a deal.I learned A LOT about the importance of vetting any professional/contractor (and verifying any proof they provide) before they start any work.

At the same time, try to work out a cash for keys deal.

Cah out can be used as an asset and for PITI reserves and a Heloc can "Never" be used as an asset or PITI reserves.I generally work out the options for my clients to compare a cashout to a Heloc so you can see payment to payment, overall costs and rate.