Many people have done a live-in flip, but you should seriously consider your lifestyle situation, for instance, if you are married with small children.

@Karen Margrave I would balance the "heaviness" of the low roof side by enhancing the columns on the other side.

I fly down several times a year to attend events with Lifestyles Unlimited to hone my real estate investing skills. 

Total he told me he owns 10 and still lives in a frugal life style.

Congrats on having this event not effect your living standards or lifestyle..

What I lack is Handy skillsWhere should I start when developing my Handy skills that would best enhance my flipping abilities?

One idea is to partner with a local expert in the city of choice (based on where you want to be - lifestyle investing, and also the underlying market drivers) and to pop in on a place that they have purchased, are renovating, and planning to rent.

In both Denver and Colorado Springs, we had numerous clients in the last two years move here from San Francisco and Seattle to get a (slightly) more affordable home and enjoy the lifestyle that Colorado delivers (@Matt M.'

Start with your end goal and your lifestyle in mind... what do you want to accomplish with investing? 

One is a financial decision and the other is a life (lifestyle) decision.Why FOMO?