Remember your costs will be more for an STR, you'll be paying for a lot of things you wouldn't with an LTR - higher STR insurance, all utilities including internet, supplies like toilet paper, paper towels, dishwasher detergent etc, upkeep on furniture and linens if damaged, yard maintenance and grass cutting/snow removal, trash removal, etc.  

So, I tried to help the situation by getting a contractor to go replace the floor and remodel the bathroom so that the house is nicer for her.

Check the MLS selling Multifamily 50% are furnished and remodeled. 

That can be remodels, rental data, PM management, and landscaping to name a few. 

. - The insurance industry like many others (including our industry of home remodeling here in Chicago) has escalated exponentially in cost.I've got several local Chicago brokers I can share with you, but I think no matter what your rates & premiums have probably gone up...I will send over a couple of contacts for you.Just curious, what neighborhood of Chicago is your building in?

But if its got at least a half bath (i.e. no tub or shower) which is what I'm guessing you mean, then adding a shower isn't too bad since it either has an ejection pit or something that toilet and sink are draining to.But once you figure those two things out.

I just remodeled it and am looking to rent it and pull about 50k out of it.  

Call remodeled comps in the area that has been bought and sold within a year 

Hello everyone,I’m the owner of a seasoned general contracting company with extensive experience in residential remodeling and assisting other investors with property flips.

My worry is the old house might be too much of a hassle to fix latter down the road and increase rent.my thought are that buying a newer one would save me remodeling hassels.