My concern is with a low downpayment and high monthly cost $3844 (PITI, HOA, PMI, utilities), this would limit my ability to ever rent out to a family if they don't allow individual leases with multiple roomates.

@Jobee Vincent Buenaventura as far as I’m concerned, there is nothing stopping anybody in this world from putting in offers on anything.

@Cristin Rakestraw I have never used these services, but my concern would be access to money when there is damage or unpaid rents.

My big concern is how can I transition a cash purchase into long-term debt and how long would that take?

A big concern is that if we don't get enough snowfall or have a bad fire season, all three units could sit empty.3.

My concern with this is I don't want my DTI to be too high when it's time to refi. 

Typically checking the Rural is a concern as most lenders do not want to lend on rural (farm style) properties as investment properties.

My question / concern is about timing. 

However my real concern is you mentioned that your bills depend on their ability to pay as well which implies that you don't have sufficient cash reserves to handle financial hiccups without putting yourself and your family in a financial tight spot. 

But, I assume you are aware of that and obviously not concerned, since you thought it was smart to "purposely" choose your wording and post it as a headline, on a public website, for the world to see.