This doesn't mean that they can't specialize in a particular facet of REI (agent, PM, contractor, etc), but I've had much better results working with partners who have some first-hand knowledge of what it means to be in your investor shoes so they can help you in making good business decisions for your portfolio, regardless of whether it benefits them in the short-term. 

In my shoes would you take the time to use the city to enforce any type of removal of the tree and pursue compensation for damages?

Also, insurance companies can deny claims for certain situations, so it’s not bulletproof.Many people in your shoes run the rentals in an LLC for liability purposes but keep their primary home out of it, and they make sure their LLC has its own bank account, lease agreements, and insurance.

Many investors in your shoes find that looking out of state for their first rental property is a smart move - markets like Akron or Canton, Ohio; Columbus, Georgia; Southaven, Mississippi, Birmingham, AL offer more affordable entry points with strong cash flow and growth potential.If you want to stay local, house hacking (like renting out a room or a duplex) can be a great way to build equity and reduce living expenses while gaining hands-on experience.Ultimately, the best approach depends on your comfort level with managing properties remotely versus locally, and how quickly you want to start investing.

Also, In your opinion, what would you do generally if you were in my shoes?

New luxury car in the driveway, 40 pairs of shoes stacked in brand new boxes, a closet full of purses, but late on rent.

I’ve also had the opportunity to help both new and experienced investors find deals that actually make sense on paper and in real life.I love working with investors because I’ve been in their shoes.

If I'm in your shoes I'm stock piling cash into a HYS account 1-2 years.

If I was in your shoes, I would probably expand the CHS property.

It will be very difficult to find a lender who won't require a personal guarantee from the borrower in your shoes- owning residential real estate through an LLC.