I have also reached out to J Scott more than a couple times, maybe borderline annoying, but his blog is a great resource and he is also very helpful himself if you reach out to him.

If you've got a long term tenant in the 1/1 and STR guests above, that might be a bit of an annoyance and cause some potential issues.

They are unbelievably annoying.

Don't pay for expensive conferences or mentor classes; 80 phone calls four days a week; block your time; do not send requests to make a phone appointment when people do that it is annoying and you will be blocked; what company are you with?

That annoying piece of garbage that kept sending me mailers relentlessly without  respect for my privacy, or that guy that only send me one mailer and wasn't so dang desperate?

That said, I could see how this could be a plus for a family who’s kids would be attending that school.Another that would not be a dealbreaker, but certainly annoying- being a dog owner on a street with lots of dog walkers!

You are making thousands of dollars and this is a risk that we all take with an annoying tenant. 2) I'd make sure that the lease does, in fact, expire in December (if not sooner).

There is one small annoyance with them since we process their bookings on our own platform.

It is slightly annoying when you are reaching over it to grab something on the island, but a buyer will not think of that. 

If you paid off the heloc and just planned on getting a new one each time, not only would you annoy the bank, you would also incur extra expense via doc prep fees, closing expense, appraisal, filing fees etc.