Point is, (a) it's all but impossible for the investment to go to $0 and (b) you have direct, impactful CONTROL of outcome. 2nd: Back to the CONTROL aspect.

Together with the equity that the house will have (heloc or refinance).No one has provided details to knocked down the idea yet, so I'm leaning in the doable direction.

OwnerRez – A comprehensive PMS (property management system) that handles bookings, guest communication, and even direct booking websites. 3.

That will only leave healthcare to be something I will not have direct ownership or control over as I cannot feasibly own a hospital, nor an insurance company.

Racine is difficult to work with (No direct contacts just general email and voicemail inboxes) but Kenosha is very responsive and easy to work with.

In my experience there are many areas that are going the wrong direction with their local landlord tenant laws.

As a few have mentioned, the best way would be to call the listing agents directly, but depending on how much time you want to dedicate, setting and going on multiple appointments with different people could prove to be time-consuming. 

I think one thing that is helpful, is to be more directed in your question and what you're looking for with regard to coaching.

@Steve EnglehartGet your retirement funds into a self directed IRA.

My sister and I founded Abideaway to help short term rental hosts increase their profitability and guest experience through interior design, mural painting, and digital branding—in essence, a suite of creative services to set them apart :) We work nationwide and would be happy to help wherever you land.Would love to chat with you to learn more about your direction and see how we can assist.