Yes Pittsburgh is a good choice for Investors who either live here or are remote as the buy-in is a lot more conducive than other more saturated markets.

Smoky Mountains seems to be a solid choice but I wonder about oversaturation and competition in that area?  

Probably not; I've done pretty well myself from them, and you're a smart and nice guy so I would be shocked if you *weren't* killing it!

You have three choices...transfer the property and keep the loan in tact hoping they won't trigger due on sale, refinance into a loan that allows it, or simply leave things as they are. 

Umbrella insurance can be a smart way to shield yourself and your partners from potential risks that basic policies might not cover.From what I’ve heard, local insurance agents familiar with investment properties in your area are a great starting point.

If you were in my shoes, what real estate strategy would you recommend for scaling quickly (but smartly) so that I can replace a good portion of the W2 income from real estate investing?

David,Yes, investing out of state can be a wise choice especially if you live in a State like CA, NY, NJ, CT where home prices are over priced and taxes are brutally high.

If selling is your priority, focusing on completing this one first could unlock the equity you need for the next steps.Your idea of forming an LLC is smart, especially if you’re considering investors.

I have one that is awesome and smart and specializes in Real Estate tax planning mostly because he is an investor as well so he is really good at what he does.  

It's important to consult with an attorney or an accountant to determine whether an LLC is the right choice for your specific situation.You can reach out to me and my team who can guide you through the process and help you navigate any challenges that may arise.