Later found out it was the owner which gave no notice to me or the tenants about randomly showing up (the owner going to the property has happened numerous times even after telling them they cannot do that and need to give me or the tenants notice ahead of time, somehow they don't comprehend that).

In searching existing STRs, it is very clear this happens in practice, but I am not willing to buy a property and gamble that we can do an STR.

I also believe that all property managers should have numerous vendors for each project/request that might come up.

Not likely but it’s a gamble versus a scalable business approach.Develop an operating agreement.  

I decided to gamble on appreciation and overbid on a duplex that will have good cash flow in Oak Park after losing another all cash deal (I bid all cash, over asking and was outbid by a buyer with similar terms with an offer “well above” mine on a different property in the same neighborhood. 

Personally, if given the opportunity to start anew, I would pursue this approach, as it offers numerous benefits.

If you're counting on appreciation, then you're gambling - doesn't matter where we're at in a Real Estate cycle.

Therefore, she's not going anywhere in May unless she wants to.I'd inform the tenant that you have incurred numerous costs with advertising and time spent marketing/showing the unit and had to decline a new tenant at a higher rent.

I had numerous electricians tell me the old knob and tube was ok, but I will be replacing all of it in the future for piece of mind.

If AirBNB were a franchise instead of a platform, they would be in violation of numerous franchising laws and regulations.