They can provide personalized advice based on your situation and help you understand legal implications or tax benefits.Potential Liability:Continuing to run all expenses through your holding company might expose you to some liability.

Booking.com is even more expensive than VRBO/ABNB, so you will likely be costing yourself money for every Booking.com reservation.

@Mindy Jensen A little too personal to post publicly but if I can figure out how to PM you I would love to get others opinions. 

Especially in a big money/high demand area like you're in.

I am an investor and I also happen to do some private money lending.

Your post is under the house-hacking section, do you plan to house-hack and live in this property that you purchase in Jacksonville.If you are planning to live here in Jacksonville, it is important to choose a good neighborhood that you would enjoy living in.I personally like the 5 points/riverside, San Marco and Southside/Baymeadows area.These areas have more resturants/activities than other parts of Jacksonville in my opinion.

Even with my income, most of my money goes to taxes.

I personally wouldn't bother with an attorney.

Tell the buyer to come up with more money down 

but that money is tied up.higher risk: borrowed money.