So I ask...What are the biggest pain points of operating a STR?

There’s a great story for another time about how I met my rockstar investor agent.The biggest challenge I faced was stepping through the fear that hit me when I walked the property with my inspector.

Even with 3% rate, the first few years the ratio of P:I is about 6:9 only.So if you purchase IO or ARM, but add principal every month, then it's not that bad actually.My biggest issue from my view is actually appreciation growth.

However, I think this can be misleading or a bit of a trap for a few reasons:- One of the single biggest advantages to owning an apartment complex is that you can scale management and all tenants are in the same location.

The other big benefit to an umbrella is it protects you against all aspects of liability risk, people get so worried about rental properties, when by farrrr the biggest risk is auto related. 

Networking has been the biggest factor in my success so far.

Plus, the bureaucracy that is New York throws a whole different hurdle at you that you should be mentally ready for, in case you do decide to invest here. 

., etc.Other than age-specific issues like LBP and asbestos, the things I'd look for on an old house would be much the same as what I'd look for on a newer house--these things would include: signs of water diversion failures (such as rot, peeling paint, masonry damage), settling/structural issues (one of my few "deal breakers"), the type and age of plumbing, HVAC, and electrical, condition of the roof, the condition of the sewer main (scope it), the type and age of windows & doors, a meth test, a radon test, etc. etc.I have properties from the 1910s, 40s, 50s, 60s, and 2000s, and frankly--the older properties are often my favorites, and some of them are the best-performing properties in my portfolio.Just being an old house doesn't--in and of itself--make a property "good" or "bad".In some scenarios, older houses can have big advantages over newer houses.In my opinion, the idea that “new houses always cost less to maintain than old houses” is one of the biggest misconceptions among inexperienced investors! 

Chicago can be a bit of a pile of hurdles.

The biggest downside for us is that a lot of our capital is tied up in our primary residence right now.