If you get those tenants out, and we get the property in good shape, I can take that property and make it a top performing short term rental on the island.

We don't know the maintenance he has been performing (if any). 

There are many different strategies that can work within real estate.I would argue that you should invest in something that you are passionate about.If you are passionate about walking, health, walking access to a lot of stores, invest in an area that has a high walkability score.Past performance should not be used as an indicative of future performance.

Not all upzoned lots are created equal - you will need to perform due diligence on each one.

Owners mistakenly ASSUME all PMCs offer the exact SAME SERVICES and PERFORM those services EXACTLY THE SAME WAY, so price is the only differentiator.So, the first question they usually ask a PMC is about fees - instead of asking about services and HOW those services are executed.EXAMPLE: PMC states they will handle tenant screening – what does that specifically mean?

Owners mistakenly ASSUME all PMCs offer the exact SAME SERVICES and PERFORM those services EXACTLY THE SAME WAY, so price is the only differentiator – and they often select the first PMC they call!

Clawing back equity for non performance turns into a legal battle far more often than just terminating a service provider.

@Tim Shanahan I have purchased a duplex for $57.5k, performed a $25k reno and it rents for $1600.

You have to consider how your current home performs as if you invested $180,000 into it today, your mortgage payment today, your rent today, etc.If you sold this house today you would have $180,000 in your pocket.

When working with a cost segregation company, they would perform an onsite visit as well as take care of all of the items you listed above.