Purchase price: $80,000 Cash invested: $145,000 Turning a 3/2 into a 4/2 duplex for short term rentals.

As others have mentioned, DSCR loans are generally for turnkey rentals (although outdated rentals may still qualify depending on the level of deferred maintenance). 

He has no legal rights to the property or the deposit because it belongs to the legal occupants of the rental.

Some of the "package rate" groups start at $15k, but include the compliance reviews of marketing assets, too.  

He is interested in REI, has good basic knowledge on REI and has more than enough saved up for down but hesitate because of current market, interest rate, rental demand, capex, first investment jitters, draw of stock market, etc, etc. 

BTW: did you check local ordinances about boarding room rentals (which this would be)?

I also want to learn how to fund my first rental property

I have each of mine under a Landlord Policy, but then have an umbrella policy over my own home and the rentals; extended liability coverage.

Which could be an open space Medical Equipment rental business, down to a Dentist's office with multiple room utility hookups.You're going have to vet this to a lower level of discussion anyways. 

Would I be able to sell 10 houses in a package and use that to buy one house?