@Phil AveryConsidering your financial situation and the current market conditions, each of the options you're contemplating has its own merits.Given your inclination to begin with a significant amount of equity, option 1 may be a good fit for your objectives.

Will it be the best option?

I think Columbus is a great option to consider.

This is a great option to bring in familiar tenants for their environments. 

You could also consider lease options which may help with your fear.

Or would their be a better option that I am not thinking of? 

Solar has come a long way from its origin and it has enabled me to save a lot of time and money.For cameras, many brands offer a solar option.

Both worth over $1MillionWe've always been insured for $1M in liability.Our broker presented an option for insurance for one property that would be $500K.Do you think we'd be at risk with this level of coverage?

This seems like it may be the least intensive, and one of the more affordable options as you qualify for more optimal loans if the house serves as your primary residence 

My Strategy:- Buy with primary goal of renting in the future- Live-in flip for the first 1-2 years to build equity and increase potential rental price Exit Options:- Refinance and rent the property, using equity and savings to buy again, move in, and repeat- Pull equity that built due to small renovations done over 1-2 years and purchase another property w/ intent to rent, staying in this first one- Sell/1031 (thanks to forced appreciation from reno)Will this work regardless of the asset being a townhome or SFH, or am I missing something?