However I am struggling to understand and evaluate the risks involved with cash out refinancing 2-5 years down the line.

For example, the iconic Malibu waterfront homes were built directly over the water, many by variance, and assumedly will not be permitted to reconstruct, certainly not with the same materials or attached architecture.

You most likely won't need to rezone, or get a variance of any sort, unless your lot is shaped strangely.

.: Thanks, Dan, but that's not helpful since it (a) involved a car, not an investment property, and (b) wasn't even used.The advice from almost every investor is to protect your investments with an LLC or umbrella insurance.

My involvement would go down drastically to where the only thing I'm doing would be funding the deals.  

This could mean either spending at least 500 hours actively involved in the property or ensuring your involvement exceeds that of anyone else, such as a property manager.

I knew this 4 years ago and decided to build my real estate portfolio to get enough know how to finally get involved.

Those things factor in the variance needed to have confidence in my estimating.

I am starting to become involved in real estate investing and I am looking between two cities in Ohio to purchase my first property (hopefully a duplex).

I personally have no connections with anyone who is involved in this niche and I'm wondering how other people have started their journey.