My main goal is cash flow right now since I have recently retired and the money coming in each month is important to me.I would love to connect with other investors in the area and get some advice from people who have had success in Charleston. 

The main question is $950 a month worth all the upfront time, and the potential increased time when things go wrong.

So I’m in a bit of a bind, I have a duplex I’m house hacking we remodeled entire thing, new hvac, electric panels, electric main, updated plumbing, water heaters, furnace, install central air, roof.

The property features two 1,400 sq ft suites on the main level (one currently leased) and over 3,000 sq ft on the upper level, with 750 sq ft already occupied, 3 small office spaces (+/- 250 sq ft each), and a basement tenant with 1,400 sq ft of storage space.The building generates $6,000 in monthly gross income from its five tenants, but with full occupancy and market-rate rents, it has the potential to bring in $10,000+ per month.Given its historical significance, stunning architectural details, and location, I’m curious about your opinion: Would this property be more marketable for sale with or without the current tenants?

His main house would be potentially one that can cash flow for us as a rental when his daughter moves out in the next year or so.

Mainly Sub2 and seller financing.  

I wouldn't expect someone in Maine to take a stab at this little town but newer investors can see what it may take to pick a market closer to them. 

From what I have read, most internet "gurus" suggest putting each property into its own LLC, 123 Main St.

The main play with turnkey rentals is appreciation and paying your loan down over time. 

In the short-term I mainly want to focus on using and working on my primary property as I feel it would be the best and most comfortable entry to the real estate world.