I have people that book for multiple weeks during season and I don't blame them for wanting a better feel of the place before shelling out $20K.  

Where I would ultimately like to end up is with multiple properties that I rent out, even on an international level, as I love to travel.In order to achieve my goal: What strategies could you all recommend?

One of the key benefits of a DSCR loan is that it allows you to qualify based on the rental income the property is expected to generate, making it ideal for those with multiple properties or who may not have a strong personal financial profile or W2.

Thanks Reese, I will definitely take a look at your posts for more information, I’ve been reading multiple real estate books in the last couple of weeks, but definitely will leverage from your experience!

Google search.Ability to buy multiple properties with minimal capitalYou'll need multiple properties to replace your income.

I’ve been documenting multiple comps close to my house tracking rents and it seems like my house would rent around $2,000/month.

Not sure the rules in NY real estate, but it's best practice to interview multiple brokers and understand what you are getting yourself into beforehand. 

This property will not compete with hotels is what I thought  We just book multiple rooms next to each other to take advantage of the included Disney transportation.

It was in multiple offers.

It can be multiple factors.