One of the main drivers of this dilemma is the low 1bd/1ba garage conversion and $30k seems like a large cost for one element of a 350 sq ft conversion. 

The numerator will include your cash flow and principal pay down.

Numerous improvements have made over the years.Dad wants sell the property this year, so I will assume it sells for $1M.Dad’s LE share would be $300,000.  

This is in spite of getting numerous off market properties sent to my email.  

I need to make my first move so as to avoid analysis paralysis but I don't know how to go about it.I hope to meet a mentor(s) who can help me with my vision to own numerous single and multi family rentals to create cash flow, financial freedom, and a legacy for my family.

For the past 8 years, I've faced numerous struggles while trying to establish a new life on my own.

From automatic marketing on numerous rental sites, to the amazingly detailed background check and the user friendly platform for both the prospective tenants and myself my experience has been great.

We're looking to build something unique/contemporary with of course elements of the local area (mountain town).

Lenders typically prefer to offer loans when the property is cash-flowing; if the DSCR is under 1, it might still be possible to get a loan, but expect less favorable terms.Understanding these elements will help you better prepare for securing a DSCR loan, allowing you to leverage your rental properties effectively for further real estate investments. 

And apart from that side, assuming the project goes well, does the cost and profit share elements look fair?