--Financing:I would like to do 20% down, or more if needed, but I would like to avoid 100% cash offers as it would likely be the majority of my liquid assets.Question: How does financing differ from the mainland?

Are you just calling for the listing, or can you offer a free report for example 99 reasons why your home didn't sell or something like that.Don't forget to call the people who know love and trust you. 

I’m eager to learn more and want to constantly be around like-minded people to keep growing in this space!

I can get you connected with PM's and the like to help you build your team. 

I don't like to gamble on rent appreciation.

More like a 101 of taxation: you had a reserve of losses -> it helps when you have profits.And a tax geek addendum:I also do not see a direct link to cost segregation benefits here.

For a new investor, events like this are a goldmine.

- Guest Insurance – Do you require guests to carry their own insurance, or do you use a service like Safely, Proper Insurance, or another option to cover damages?

They didn't pay for it, so they don't take care of it like an owner.Before you make assumptions about costs based on a seller's contribution to improvements, find out what they improved? 

Anything below is likely in a bad spot.