I ended up having to get a state fund work comp policy for $5000 which I think is the minimum amount regardless of scope.

I am hoping to pull from a HELOC soon with funds up to approx 125K available to me through that.

3) Your $250k with 30% down => about $750k (you also need funds for closing costs, taxes, etc.)

I just bought a $400k STR and the break even point with 25% down is $54k with a 2% sinking fund and 3% maintenance built in. 

Selling multiple properties in a 1031 exchange to consolidate funds for one investment property is allowed, but the property must initially be used solely for investment.This post does not create a CPA-Client relationship.

Then can decide for whatever reason not to fund the loan and keep that engagement fee.

If your 5th deal is good, you should be able to find funding outside the banking industry.

My plan was to keep the condo as my residence, but after a year, refinance to fund a down payment on a multi-family property, either out of state or in the surrounding NY area.

I have a pretty large emergency fund in place for those properties, but I wonder if that capital could be better employed elsewhere (potentially acquire another property).  

You may find that the payment was made directly to the tenant; you may find it has not yet been funded.