If it's as close to downtown as you say, I would bet that they are already owned and not on the market.

@Arturo Colmenero you could try referencing zoning maps to look for multi family pockets but your best bet would be to subscribe to a service like Reonomy for example if you’re serious about finding multi family properties

Proving to the carrier that the building is a lower risk through methods like the wind mitigation report is your best bet to get a lower price without sacrificing coverage. 

I'd rather bet on myself and live with the consequence than throw money out of state and lose most if not all control. 

If you're already willing to be 300 miles from a rental, I would sell that sucker and use the funds to purchase a wholeeeeee lot of higher cash flow out of state stuff with financing.

I bet he/she came come up with some great options.

-based consultant Eilers & Krejcik, predicts that sports betting in Kentucky will go live as early as 2021 as part of a wave of 16 states that includes Indiana and Ohio. 

I would bet he would be willing to pay more for the place because of his past and knows how hard its to find a place. 

Honestly, your best bet is to actively network, read books (boring and interesting alike) and listen to podcasts to develop your knowledge.

But would I bet a super-high end rehab on it?