You skip much of the zoning, getting through city hall planning depts., etc. that you have to do for a larger tract you want to subdivide. 

At your price point there's a few areas that you could get into, but you'll need to keep in mind you'll need to have some extra funds for making any renovations you might need to maximize the property. 

Wholesalers asking too much.

The property is owner occupied, with no residential renters, and no commercial renters, what type of property insurance is needed here? 

I'm tired of sitting on the sidelines and feel I've started to fall into the "analysis-paralysis" trap I hear so much about.

Leverage can be a great thing but its a calculated risk , and a lot of people put too much faith on the upside and little consideration  for the downside .

If so, how much?

You can also look into an umbrella policy for higher coverage but not always needed. 

Hi Jeremy,You'd need to look for a commercial multi-family loan.

There are lenders who will let you pull out 75%-80% or so, possibly based on rents vs your own income if you don’t qualify that way, but their rates and fees will typically be higher than conventional loan products, and you may need rental history to go that route.