I wouldn’t plan on it heading to a solid B in the next 24 months.

I would have a conversation with them and if theres not a clear root cause then switch to another PM company.

I am trying to make sure I have a solid budget setup for next year.

If there's a solid property manager where your rentals are located and they don't let things fall through the cracks as many of them do, I would advise hiring them so they can enforce the rules/law so you're not unhappy. 

You may only break-even in the beginning but over time, this will be a solid winner.

I currently own a rental property (it was my first home purchased back in 2011 so I have a solid chunk of equity here) and my current primary residence which I purchased last year.

Looking for recommendations for a solid tax accountant.

From what I have read and others have echoed, have a solid cleaning crew (back-ups when you need them) and a handyman.

those are some solid numbers.

At minimum I’m thinking:*General liability*Personal injuryPossibly thinking errors and omissions but that may be overkill.Please let me know your experiences and if you worked with a solid insurance company, both on island and off, as I will appreciate the feedback.