With respect to comping it, yes I think that may be difficult.  I

What you are overlooking is that you going to need some skin in the game...its usually called MOOLA...

You are possibly leveraged too high to make this deal with lender. they may be skeptical, because you may not have enough skin in the game(YOUR MONEY) some one financing the down payment is normally a no from a lender on investment property

Make the payment similar to his rent so you know he can survive and pay on time .I’d rather have the guy give some money down so he has skin in the game . 

Can we start a list of Mastermind groups - both small and large - to help others like me who are having difficulty finding the right one to join? 

But if you have thick skin and can deal with some BS, there’s money to be made there. 

Before you continue down the modification path much further I'd get in touch with someone who specializes in garage conversions or ADUs and get an approximate price and timeline and run the numbers again, it seems like you may be underestimating the cost, time, and difficulty of a project like this.

Just a few ideas, but there are a million ways to skin this cat, it's exciting to think about.

Set up a holding company LLCSet up a SLLC (Series LLC)Since securing a conventional loan on in an LLC is difficult, I should buy a house in my name with a converntional loanTransfer from "Eric" to "land trust"Transfer from "Land trust" to "SLLC XYZ"???

Getting comps is very difficult. I