I am wanting to push myself further out of my comfort zone.

Make sure to check with the local zoning office to make sure that short term renting is legal..

If you want to get ahead of the game you can check the zoning yourself to see if its even possible to do so.

I like the thinking with the duplex, hopefully the zoning allowed for it. 

Doesn't mean someone won't come along but being in the red each month isn't easy I know. 

Also you could go outside of your comfort zone and buy in a more affordable area?

Here are the details of the deal:The parcel info shows that the lot is zoned for multi-unit but the current use is listed as a single-family home. 

They should have help files that instruct you on how to screen an application and red flags to watch for.You collect the security deposit via "certified funds" which means money you know is good.

Does anyone have any knowledge of zoning /city laws that would prevent me from doing this or would permitting process be relatively easy with a good contractor?

@Gary AbnerYou have to watch out for zoning codes.