So the real answer is do what's comfortable for you and what makes sense based on your own financial position, your age, your desired outcome, and your local market.

You should engage with the local players in the commercial market i.e.

I am debating using my local lawyer vs. finding a lawyer in the state where the property is located.

I can also put you in touch with local lawyers if needed.  

Current ownership was not local, and didn't have a presence anymore.

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.

Hey Nathan, I'm a local broker and PM.

A client of mine recently invested there and raves aboutt the ease of finding solid contractors who stick to the budget.One piece of advice: before jumping into any market, spend time understanding the local economy, demand drivers (like job growth and population trends), and the landloard laws.

I hit up a local wine distributor and pickup wine boxes (wooden ones) they give away to anyone who wants them.

I recommend you research the local section 8 program.