Keep in mind many HELOCS require you to bring them to a zero balance at least 1x per year so if you are not prepared to do that somehow with your Option #2 it may put you in a bind.I like #3 so long as the numbers make sense in keeping your current home as a rental (and don't over leverage...). 

The following week I'll give $600 on Monday, and balance due on Friday. 

I work with our of area partners, they provide the down payment and we get a banks loan on the balance.  

Balances out a little .

Actually, at least on the streamline, they give 50% of the Reno to the contractor up front, with balance upon completion, which is generous. 

Any additional payments go directly to decreasing your principal balance, which jumps you ahead in your amortization schedule and can save you a boatload on interest. 

If at all possible, I would absolutely open all three of the second floor windows, it creates a nice balance and provides interior light.What the building lacks is a residential, attractive and welcoming entry, which will completely transform it without spending a fortune.A few questions... does the front property line extend to where the grass strip ends at the alley?

I just seller financed a commercial property for a buyer who  put 25% down, and he's paying me 11% interest on the balance with a 2 year balloon against a 15 year amortization.Second owner finance situation is when conventional financing is not available.  

I am looking for anyone that can offer advice on the secret to balancing all of these successfully.

If that has not yet been addressed, that too will come up in the inspection and need to be addressed.You may want to consider selling it to a buyer with a downpayment and carrying back a note for the balance.