If anyone has any experience or suggestions, please jump in!

I suggest you always have an assessor come out to take measurements.

Hi Stephen, I would suggest reading as much as you can and connecting with people in the industry.

I would suggest you start looking into South Eastern Wisconsin.

One thing I would suggest is if you start getting some consistent bookings do not jack your prices up over 15% as a new listing.

Hey Alejandro, I would suggest Ohio or Indiana.

Given that I am a complete newbie...what would you suggest? 

In addition, the company that they recommend we work with, Prime, helped me set up my companies and though I repeatedly asked them if there were any differences in how it was set up because I was a Canadian, I was told that the way they suggested I do it was the right way.

I walked all the nearby comps, gave the seller my opion/list of what his property was "missing" (fenced yard, light staging, add a 3 board fence panel and landscaping here...) and advised him to get a surveyor to mark the lot corners...The previous agent had not suggested they get a surveyor to mark the lot corners when he bought the property to flip....there's a chance the house or driveway may encroach the neighboring property.  

I would suggest buying another LTR where you are and then next, pull out some equity to purchase a MTR property.