I know building a reliable local network will be key, so I'm hoping to connect with experienced real estate team in the area.The military presence in Jacksonville catches my eye, and I'm particularly interested in properties that might appeal to military personnel and the associated contractors.

If you have high W2 income, the amount your STR makes (or loses) will be peanuts compared to the tax savings.

I really like LLCs compared to corporations because of the free stepped up basis for passing property to my children. 

Also, I believe the tax benefits are horrible compared to the states, but I'm not too sure.

With some more math, you’ll see that the extra amount in dollars is not that much compared to the total amount of interest paid.

We recommend you get management contracts from several PMCs and compare the services they cover and, more importantly, what they each DO NOT cover.

The BEST lenders I have ever worked with (as a borrower) are, as you say, quick to respond, reliable, honest, and never leave me hanging. 

In addition, condos tend to not appreciate as fast in value compared to single-family or multi-family homes. 

I'd be happy to get you some rough terms to compare to other options that you have, but I also agree with Jay that you should be wary of just selling and loosing that equity that you've built up in the property.

It sounds like you need a reliable and trustworthy partner to help you navigate this transition seamlessly while keeping your solo 401(k) on track.I’d highly BiggerPockets Partner for this, Equity Trust, a top-tier custodian in the industry.