It's honestly hard to believe that data is so inexpensive to get these days.

All in all, I’m at about $3000+ in expenses in 2-3 months of ownership, not counting whatever the cost of central AC issue is.

What are some non traditional but inexpensive ways to fund a deal?

The house is over 70 years old and I understand this is "normal" with an older house however I wonder are there any relatively inexpensive fixes (less than $4000-$5000) for this problem?

And finally, with the money being as inexpensive as it is, this is a great time for leveraging, which automatically increases cash on cash returns.

I've spent most of my time here on BP arguing that this is 100% FALSE ... you can still make profits investing in RE in expensive markets, and in my last 15 years of experience doing just that it can actually be MORE profitable investing in expensive markets.

If negative cash flow, how much in expenses (especially mortgage interest) will you be paying?

You can use Hard Money lenders, private money, your own saved money or even start with a deal that is in a relatively inexpensive market so the cash needed is low. 

Logic says I'm going to pay 3000 in expenses, soon enough, if I keep negatively cash flow like I have now.

Assuming 50% expenses and spending the rest on PITI can get you in trouble.In the last 5 yrs my duplex has averaged over 76% in expenses per yr including capital improvements.