With no experience or funds to get going on this solo (currently a bartender), my thought was to join someone who is already doing it and learn along the way.

What is the current interest rate on a private money loan approximately $300Kthanks 

My spouse and I moved to Ohio last year and we're currently renting in Akron, with the goal to househack by the end of the lease, or sooner if we find the right property.

I currently STR the two units with a plan to only STR one of them once I build the extra unit. 

I currently live in Cape Cod Massachusetts.

Currently, I live in Hawaii, house hacking my own property, and am looking to expand into out-of-state long-term rentals.My goals now are to master the art of wholesaling, continue raising private money, and build a strong portfolio of long-term rentals.

Trying to get into the nuts and bolts of how he was trying to source a location, project size of preference, what type of financial modeling he does, what kind of tenants he was hoping to attract/the strategy behind it, if he was doing any joint ventures or had done any in the past, if he had taken part in any syndications, what management strategies he was implementing with his current properties to maximize lease uptime and profit, what types of leases he generally favored contracting for his properties--all of that was like pulling teeth.

If you're doing a rate and term refinance, there's typically not a seasoning period but again it's common for lenders to require it be rented first.If you're doing a DSCR cash out refi, it may not need to be rented first but you're probably paying a higher rate.Your best option is to call a loan broker you trust and go through the options based on your current situation.

I currently have a policy through Hudson Insurance Group where my LLC is the named insured and my properties are covered therein.  

The refi, worth current rates will severely inhibit your cash flow.