The property is currently doing two long term rentals and I live in the 3rd unit, but I plan to convert two units into STRs this summer.

Make sure you start mapping out plans for your investing journey, as well!

Hey Tom that is part of our plan once we have a working prototype.

Agreed, $50k~ does not go very far as a 20% downpayment in St Augustine lately, and although you mentioned you have a higher risk tolerance, that would be a lot of debt you would be undertaking between margin, your existing rental property debts, and the new debt with the planned purchase.

We plan to convert the sale proceeds into multiple properties to create passive income. 

Tenant just informed me they plan to vacate the property tomorrow (so, 24 hours notice) due to "the business growing and the space now being too small for their needs."

I learned always to have more than one financing plan.

I was planning on renting out the the living room as a bedroom.  

If you were buying a 2-4 unit in your personal name and planned on living in one side, you might be able to get 10% down financing.

It's worked great for us the past few years and I don't have any plans on changing systems.