This being your first deal makes it a gamble but if you're really able to get the building at that price you can borrow hard money for the purchase and renovation.

I see some properties that could be absolute gold mines if it were too go that way, and if not it's a small cost to pay as a gamble.

It was out of state and with as small as it was I took a gamble and did not step foot in it until i owned it, but I had the local realtor go thru and do a video and a basic eye ball inspection and felt confident.

You can gamble on appreciation, but you aren't going to pay your bills or earn a good ROI on Milwaukee properties at that price point.  

I guess that's part of the gamble, though, right?

This is neither right nor wrong but a gamble that you and your husband need to agree upon.

Insurance is just a gamble. 

At best its a semi-educated guess, at worst its gambling. 

Foreclosing after 2 years isn't the easiest and is a gamble.  

If you are looking to live in the property for a period of time then sell after hoping ("GAMBLING") for appreciation admit that to yourself.