That would be no money out of pocket and cover the 2 months or so (seasoning period) of home equity loan payments plus a little reserves.

If you are replacing the main service as well, they need to pull a temporary pole as noted by @Aaron McGinnis or use a generator.

Looking at a potential real estate investment and I have all the cash flows (after debt service) and anything else I would need I am just lost on a couple of things I am being asked for...

Even if I was able to find someone, I would likely be paying one month's rent for the service, which means thousands of dollars.

If he is legit, then he shouldnt need anything from you up front (maybe a small $100 application fee at most)Use an escrow service.  

The bureaus will allow payment services to report though so here is a link for the ones that currently report to Experian:https://www.experian.com/rentbureau/rental-reporti...I have heard of Rental Kharma that charges a fee to report just your payment but that doesn't include any payment processing.  

I still work in education, the salary helps me out qualifying for mortgages and I can save all of my cash flow and build up my reserves.

As a Realtor I have certain minimum services I need to perform on behalf of my client and one of those is presenting all offers in a timely manner.

I agree with what everybody has said so far, I would also add offer concierge services that you can charge extra for.

In my opinion it is cheaper for you to list your properties through a broker that offers Flat Fee MLS listings services.