I wondered if a fix-and-flip is a better option in my case, where I can use proceeds from the sale as seed money to pay off the HELOC, rinse, and repeat; but I can see how that would get into an endless pattern.

Some agents want the full deal...office, nice office, training room, full range of services like title, legal, accounting, marketing, transaction coordinator, insurance all in one stop shop, runner to put out signs and lockboxes. 

Your cleaners can handle most of the task you have under "runner".

You will never catch everything before buying and real estate is an endless learning process but by catching most of the items the small little things won't take down the investment.Each type requires more or less work for return and a different loan structure.

I'm always amazed that there is an almost endless supply of RV/boat owners willing to pay $50 for uncovered parking (basically a patch of gravel, not even pavement) or $125-$150 per month for a roof and one wall.A friend of mine was looking for a storage unit recently and only opening was 25+ miles away from his hometown. 

As a colleague of mine once said, "Property Management is just an endless opportunity to drop the ball."

Endless business opportunities if you are both willing to co-operate.

Agree with most of the advice here... stick to the free content (there's endless supply) on this site, as well as the podcasts.

Ryan, absolutely the questions could become endless.

Looks like a good plan, it does seem to be an endless choice.