Not as awesome as the first but more relevant.There you are a successful filthy rich investor making a lil day trip through the Caribbean seas on your fancy yacht when disaster struck.

If you are just rolling the purchase price and rehab costs with less than 6 months seasoning then you would be able to get traditional financing at a decent rate. 7.5 seems really high.

Bookings are down across the across the board for STRs this summer season.   

Season the property for 3-4 months, then do a 65-75% Cash-out ReFi. 

Also after 2019 tax season I will have two years of self employment to include on future loans.

I know that peak rental season is during summer, and most lease are one year long. 

There’s no problem anticipating that rentals will provide for your family there’s 3 things to consider:1) legally set up operations so that your beneficiaries can simply continue them without any kind of weight of going through probate (other wise a little life insurance for probate season can be helpful- this should really be a conversation with your lawyer if you have questions about probate - thankfully @Pat L.’s doing the right thing with the trust).

A property will need to season 6 months from point of purchase in order to get a traditional loan if you are considering to get cash out.There is always a risk that a lender can call the note due in you add it to an LLC but that's a limited risk. 

Someone below or above in a thread mentioned they were lucky enough to get on a call from a seasoned investor.

I then put in the pricing for on season off season etc and let Excel give me an average price.