This is desirable/necessary for overall security.All the technology must be integrated and operate seamlessly in the eyes of the guest.

I know that if you rebate your commission to a client....it is not considered taxable income for the client....but rather a lower purchase price in the eyes of the IRS.But what if you are your own client?..

@David ChanceI live in downtown Frederick and invest here too, with rental licensing that just pass in going to be even harder.Lets catch up or have a coffee

Make sure you pay on time, keep insurance perfect, head down, eyes on paper. 

Maybe meet with other investors and see if you can find someone to partner with to be your eyes and ears on the project.Is this area considered desirable, given its location between Milwaukee and Chicago, and proximity to Lake Geneva?

This is one example of a 1-2% area, I am sure there are others, keep an eye out for satellite areas if this is the cashflow you target. 

Yes, it can feel like "wasted" money on months where rent is auto-paid and there is no maintenance to be done, but when you get a bad tenant or two or when deferred maintenance finally catches up to you, they certainly earn their keep.At your scale, you might be able to get a bulk discount with a good PM, especially if you can show how well your current systems are working and how they'd be needed less than usual.

I’m looking at a similar strategy as you, starting with a small investment first — but I’m eyeing a larger investment in the future for sure. 

I am an investor in Tennessee and North Georgia, and have had my eye on NC for awhile now.  

Thanks for catching that, @Michael Baum!