Portage Park is definitely a prime-time Chicago neighborhood @Delroy Watson! 

Make sure the zoning, local building department/regulations, and neighborhood allow you to put a tiny house on your property and rent it out.If that is not possible, using that money for the next property makes sense.In general, I think increasing housing density will help provide more badly needed housing affordably.To Your Success!

I want a resort style feel, clean neighborhood, golf carts, and pool a plus .

It's all about the neighborhoods you are investing in.

Assumed nothing could possibly go wrong in the next 5 years what you want when you look at an investment property is to know the current rental amounts, specific expense items, and conditions of the building, grounds, and mechanical systems.  

This is the reason homes are so much cheaper than cost to build.

In addition to just posting your property on furnished finder, they were reaching out and building connections with hospital HR departments and recruiters to help place nurses in properties.

I imagine others don't like that it's in an older condo building without private laundry.

Our downtown isn't big, but each neighborhood has a different feel, and we have affordable suburbs if you want to be close but not IN the popular areas.

Those tend to be the neighborhoods that are gentrifying.Unique stuff to Pittsburgh I would say is don't go based on zip codes since one zip code can be composed of multiple different areas/neighborhoods.