Unsure about STR regulations in Charleston but I would advise you to search "arbitrage" on this forum and read up on the hundreds of pros and cons responses here before diving in to any market using the arbitrage model.

I am curious what your research concluded!

@James SillsFrom my experience working with investors, transitioning from residential to commercial real estate (CRE) is an exciting and achievable goal with the right foundation.

And you would get to indefinitely defer all tax on the gain from the sale.

What matters more is how easy can you get there, how often will you be there to learn, how good is your team. 

Quote from @Kevin Upton: Hello!

Quote from @Alex Moazeni: You are making the common mistake of allowing a tenant to push you around.This is your property.

Look for some of those to go in as an LP (limited partner) and learn and grow your knowledge, skills and investment money so you'll be ready for the next accredited deal. 

This would also allow you to get better pricing from lenders.

I do want liquidity to invest elsewhere which is why I'd like the cash back from the reno ASAP, but I don't need liquidity equal to the value of the house--just the basement build-out, if possible.With option #3--how do you "cash out immediately"?