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.

I didn't see your post until today. 30 - 45 days should not be an issue.This is the reason why I personally have built a buyers list of qualified buyers who can close with cash in 10-15 days (its never really that short between sorting out title issues, sending contracts back and forth, etc.)I feel comfortable telling the seller that although the contract says 30-45 days we can more than likely wrap the deal up in 10 - 15 business days barring any unforeseen circumstances.@ Tommy - I took a look at the cost of those leads. 25 leads a month for $150?

We develop a comfort zone, and if the risk is outside what we’re willing to consider we reject that investment without even needing to consider potential upside.8.

When looking at violent and property crime rates, I cut out some markets because I felt their crime rates were higher than I was comfortable with.

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. 

I'm not saying to be there friend, just be an advocate to having a nice comfortable and safe place to live.  

So, it all depends on what you are comfortable with and your investment strategy.