Last short term rental we put on the market was booked for a 30 day stay first day on the market.

Quote from @Srikanth Kumar: Hi Everyone,I’m relatively new to long-distance investing and am exploring the purchase of multifamily properties in Cleveland.

Lastly, what other considerations or resources can you think of that will help me understand the process and feel more comfortable as a first time home buyer?

Not many people are excited to see long-time solid neighbors leave and have them replaced by a short-term rental. 

Narrow the list down then, last step is make the time and go tour them. 

All of which, I’ve purchased within the last 4 years.

Deciding whether to sell or keep renting really depends on your long-term goals.

As long as you're filing jointly, both meeting the 2 yr use test, and either meeting the ownership test, then the full $500k can be claimed. 

Additionally, while rates aren't historically bad right now, they are higher than 4-5 years ago, and they will be even higher for you as an investor than they were as an owner occupant, which is what you were when you bought originally.I get that you are anxious to add to your portfolio, but that could be achieved without touching your first golden goose.Sometimes on BP, the push is to leverage every last spare penny, but that can be a risky game as the markets shift. 

The hurricane exacerbated the already long permitting timelines but the city was working on hiring more inspectors and others in the building department to keep up with the building boom we've seen over the last several years.