ARV is in the $450 - $485k range. 

I also worked in the university writing center both during my schooling and a little post graduation, so I'm fair on the English end (so long as I'm using a full size screen and a real keyboard- thumbs and tiny letters do me no favors).I have worked off and on in home repair/renovation for family for most of my life (houses ranging from new construction to a 160 year old victorian).

Find like properties and look at their calendars to get a sense for nightly rates and occupancy.Keep in mind that cleaning fees are a pass through cost to the guest.Other costs like taxes, insurance, and bills you can estimate ranges with some level of confidence if you ask around or build relationships with agents/investors

I would also check the job diversity of the city and how diverse the industries are for a little more stability overall.

I think a duplex in that price range would be difficult but not impossible necessarily.

Thinking about snagging a STR withing the 4 hour range of Vegas

I know there's a whole schedule of potential LTV ranges for SFH vs 2-unit MF vs 3-4 unit MF, with this also changing by OO vs pure-investing status. 

This will help dictate what price home you can afford so that you can let your realtor know what range you should be looking in. 

The two reasons I personally like the Chicago market is the wide range of prices and the amount of old inventory that needs to be renovated.  

Hi @Erika Torres, I'd definitely recommend getting pre-approved first, that way you know the price range of the properties you'll be looking for.