We hired a company to replace the old boiler, pains an extra 10k to do it right with expedited permits etc.

You’re right, the $1000 shortage in the security deposit is a huge pain in the *** to fight over.  

This can work well if the buyer is sharp enough to execute the transaction without full representation, but it's inadvisable for anybody but an expert.The agent can request in writing that he be allowed to work as a "disclosed dual agent". 

I agreed, he hugged me as I laid in bed on pain meds and then he left.Fast forward to two days later when I'm checking our employees work (we had an employee from the UAE working 40hr/week for us making phone calls on multi-family properties in-town) Let it be known I didn't have my phone the entire time I was in the hospital as it was stolen and wasn't allowed visitors due to COVID.

Totally possible I'm missing something there, so apologies if so, just want to save you the pain I have gone through in the past with over engineering fairly simple procedures.

I manage about 30 tenants, so collecting rent plus all the utilities would be such a pain, it's not even worth the time.

Its painful but it's a great way to get started.Unfortunately you need to be willing to do what others won't but if you do the sky is the limit :)

Obviously there is a benefit to owning a home and having the great cash flow by renting rooms BUT renting to friends/family can be a pain.

But I had to go to 2 tribunals for landlord tenant act and boy was that ever a pain in the ***.

I was overseas so it was an even bigger pain to try to sort this out.