I know the detective didn’t even bother talking to them when I filed my report.  

They bought a new dryer and didn't bother looking up the electrical that was in place, that is on them. 

He just told me to read the Cook County Residential Tenant Landlord Ordinance with the idea that doing so should just stop me in my tracks from bothering with rental at all. 

Using automation can certainly help at scale for easy things, but if you have one STR and can't be bothered to respond promptly to your guest, I can guarantee this business will not go well for you.

Yes I could do a generator but that is more bother, tell the tenants to turn on the fireplace.  

Sometimes it's ambiguous, but even then, why should I bother with the company that has numerous unresolved lawsuits, versus another company that is virtually the same but has none.

No offense but you'll never convince them and I wouldn't bother trying.

Then definitely keep reading for explanations.Should you even bother?

One thing you may want to consider is some sort of umbrella insurance - that might be a cheaper option, I'd price out bother.

I never bothered to try talking to a lender because my credit score isn’t great and I’m self-employed.