Keep in mind, when I have a bad month or an eviction etc it would be very painful if I was only relying on my rental income.   

Property management is a pretty painful industry similar to general contracting... no one ever calls to tell you how grateful they are that the heat is working lolHere in Illinois, the answer is yes or you at least need to have a managing broker on your team as JW mentioned above. 

License bed transactions can be a real pain.

For them, it was painful. 

And that's what they will do, keep kicking the can, avoid painful realities, inflate inflate inflate.

That's a pain but can be done, though you'll have complaints in Spring and Fall about it being too cold or too hot.

Realize that the eviction process can be painful but it is also likely that the tenant when they receive the notice to quit will find a solution. 

See what their pain points are. 

I would recommend finding a large developer to learn from or partner with so you avoid a lot of the painful early lessons. 

I am a repeat founder and data nerd eager to build a new venture in the investing/data space.I was hoping some (or many) of you would be comfortable sharing pains in investing that you wish went away.You know, things that are so frustrating that you'd pay to have them stop.