I've identified a small mixed use building I'd like to purchase.

Connect with a property manager, and build a list of good contractors.

Haircuts are the third building to the left.https://www.youtube.com/watch?

What key factors should I be considering, and what questions should I be asking?

I'm looking to build a STR in Terlingua, TX close to Big Bend National Park. 

They told us the price - we negotiated and We bought it, year later we knocked it down to build our dream home.Goes to if you don’t ask, you won’t get a yes.

I had zero desire to build a bunch of rentals this way..

So I would like your advice.My idea:My sister and I would build a fourplex together and finance it as owner occupied.

I've included an example below to help illustrate this.So different lenders have different rates (which do vary even for DSCR loans) but these are factors they all consider.See example below:DSCR < 1Principal + Interest = $1,700Taxes = $350, Insurance = $100, Association Dues = $50Total PITIA = $2200Rent = $2000DSCR = Rent/PITIA = 2000/2200 = 0.91Since the DSCR is 0.91, we know the expenses are greater than the income of the property.DSCR >1Principal + Interest = $1,500Taxes = $250, Insurance = $100, Association Dues = $25Total PITIA = $1875 Rent = $2300DSCR = Rent/PITIA = 2300/1875 = 1.23If a purchase, you also generally need reserves / savings to show you have 3-6 month payments of PITIA (principal / interest (mortgage payment), property taxes and insurance and HOA (if applicable).

As Mark Simpson says, you're building your house on someone else's land.