As far as whether to approach them with or without an agent - approaching them directly without an agent can save the seller probably 2.5-3% of fees, which give you some room to negotiate on the price, but you need to be confident that you are capable of evaluating the property value, estimating on the amount of work that is needed, knowing how to negotiate/ structure the deal, and navigating the closing process.

We are seeing big increases in HI because of the natural disasters in FL, CA, etc.

Became a real estate agent after I fell in love with home ownership processes and out of love with my 9-5.

The existing number of vacation rentals are so far over those caps that anyone who gets on the wait list today will likely wait 5-10 years before they're up for a permit.I do think this is the natural progression of what is still a relatively new industry.

I recommend homing in on what MOST vacationers are looking for in a specific market and try to find properties that have natural features/amenities that are scarce.  

I'm in the process of all my research and just want to learn all I can so the more information I can find, the better. 

Any HML will want answers to those questions plus a rehab budget before getting you a term sheet for a fix n flip loan for this property.I close these types of loans all the time, if you have any specific questions about the process don't hesitate to reach out.

Quote from @Nate McCarthy: Quote from @Tim Delaney: You have a lot going on there and I’m not sure I fully understood your thought process.

If your current deposit already equals one month's rent, you can't request additional funds.Keep the lines of communication open with your tenants, explain the process clearly, and you'll avoid any misunderstandings.Good luck!

In the process of analyzing deals, I reached out a property manager for his fees.