BUT, to accelerate wealth building the investor needs to be open to strategies, tactics, investment types OUTSIDE their “comfort zone”.  

I am preferential to medium/long term rentals so my exit strategy would not be applicable for many years.I make a comfortable living and have a surplus of money saved up but don't want to liquidate my entire savings accounts so I can get just one singular 200K property that may cash flow for a couple hundred bucks over the next few years.Am I missing something or being overly cautious?

There are so many different opinions and mine is just another one of them, so take it or leave it, the beauty of it all is you can do what you are comfortable with and what will work for you!

Hoping to buy one property by the end of this year, 2 next year and to scale up.Neighbourhood: Class B or C+ neighbourhood.Rehab: Comfortable with cosmetic and upgrades to the property but not a whole tear down gut job. 

Make sure you are comfortable with who they place in your property! 

That’s the most direct path to getting comfortable making investment decisions, alongside connecting with a few local agents in your area. 

Its much more challenging for single family investing so consider living in a two fam to make yourself more comfortable or just buy an investment and stay in your home. 

They stayed nine years and are clearly comfortable with the rental.

What are YOU comfortable with? 

Housing prices in Beloit are definitely cheaper than Janesville, and Janesville is (for obvious reasons) significantly cheaper to invest in than Madison.Can't be of help to the property management part though... we've looked and looked but haven't found a company we are comfortable with... your best bet there would be to join up with the Southern Wisconsin Landlords Association and network for a quick recommendation.