I guess the concept is that 1 or 2 is quite manageable and once you get over the 10+ hump you've scaled your business and have solid processes in place. 3-10 is where you have to grind it out.

He mentioned cost of fixing it up was a challenge so maybe the $10-15k I have will be what he needs to get over the hump.

Not that I have experience in corporate sales, but I would definitely think if you have experience in sales... you're probably over a lot of the humps that people transitioning to full time real estate agent struggle with.

He wants to partner with us - him being the financial partner and us being the managing/landlord partner, owning a rental unit together.This sounds like a good idea except the worry of the potential for family problems that can happen when money comes in the picture which I would hope wouldn't be an issue.

They saw my guy doing the work and us being one of the only houses dry (and at the lowest worst point for flooding) so now he's doing other people's houses. 

These are steps that let us be better PMs and helps to assure the landlords are also taking care of business (they hired a professional for a reason).

@Jimmy Watson It could be that the slab has some dips and humps in it.

I was wondering how people get over this hump - even for single investors.

Looking forward to living life with my wife and both of us being able to do what we want when we want.  

I personally envision us being in this position for a bit longer, especially going into the winter and having the seasonal slow down.