The house is actively advertised and I have multiple applicants at this time who want the place in 2 weeks. 

I would get multiple bids and ask the contractor to list the material and labor separately.I would suspect that material for gutters is pretty cheap so you might think about doing it yourself as it would not be a hard job or take too long.

A seasoned investor that has done it multiple times. 

I just want to hit this question with multiple angles so I understand how to structure the deal in an educated way as oppose to looking newb(Although I am).

@Justin Lee I got a home equity line and used it for multiple small conventional FHA loans.  

We have ran all the numbers multiple times and the property cash flows (from what I've been reading that is hard to find in SF).

It looks more like a long driveway but there are multiple properties using it.

Once adopted by state regulators, these standards will represent regulatory requirements for state-licensed non-bank mortgage servicing firms. 1 PROPOSED REGULATORY PRUDENTIAL STANDARDS FOR NON-BANK MORTGAGE SERVICERS The non-bank mortgage servicing industry is diverse, ranging from small firms with straightforward operations to large complex firms with multiple business lines.

How do you fund multiple properties?

I have laid out a rough draft plan that should allow me to acquire 35 rentals ranging from purchase prices between 65k-100k by the time I turn 31 years old with rental rates ranging from $850 up to $1300 a month (putting at least 20% down on each home with a conventional loan, depending on the condition trying to get a conventional rehab, and using the positive cash flow to pay down mortgages/use towards down payments on more rentals) I have read multiple books from millionaire investors such as Manny Khoshbin, Donald Trump, and the like.