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?..

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

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. 

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.  

I do plan to hold it in an LLC, have good insurance and umbrella as well. 3) Older homes in PS - most of the homes in PS are built in the 40s-50s and for those that own them, do you constantly run into issues with major ticket items - plumbing, electrical, etc (things that are not visible to the naked eye).

Without some on the ground knowledge those really low prices in some of the neighborhoods can really play some tricks on those "out of state eyes."

And, as it relates to your plan, you probably know the optics of your market better than I, but I find that five unit properties are often slightly less desirable than four unit properties, simply because buyers can no longer use conventional financing for five units.