You need to experience at least two complete market cycles to have a proper perspective. 

Cannot sell right now either, I am pivoting my research in the Florida market to invest and potentially purchase a property for STR in 2025 and I had a few conversations with mortgage brokers to get some insights. 

I have a vacation home that has no mortgage and we are trying to pull out equity from it to purchase another property to use as a rental and vacation spot. 

With my current mortgage + HoA at $1600, and my rent at $2700, I have cash flowed around $1100/month since moving out in January of 22.

The value I was able to add to this deal, was mortgaging the property to provide all of the cash to the seller.

Live in the converted garage and rent out the other rooms house that cover nearly all the mortgage.

based on what I looked at with the calculator the mortgage is around $2400 monthly not including extra fees. if rent is around 2000 a month you'd definitely be under.

Mortgage as opposed to Deed of Trust.

But, I am considering buying a home 300+ miles from me that I can use as a vacation home for myself a few weeks a year and do short term rentals the rest of the year.Question: Can I get a second home/"vacation home" mortgage (10% down) when I don't have an existing first-home mortgage? 

This includes mortgage payments, property taxes, insurance, maintenance costs, and property management fees.