Your major concern will be handling the locks solo, but that isn't hard if you set up your boat correctly. With the mast down, you will have to come in and go about 2/3 up the lock on the side you have prop walk. Probably will walk to port, but check ahead of time.
Pre-rig a long line - 35 to 40 feet long. Tie at the port stern cleat, then bring to your middle cleat and take the line through the center cleat hole and bring to your port winch near the companionway. Tie to the port lifeline even with where you will exit on the port side just forward of the helm. Make sure the line glides smoothly through the mid cleat hole. I use 1/2 inch nylon. Set up fenders so you won't contact the wall.
Slowly come alongside the lock wall and use reverse to stop at the bollard. Loop your line once around the bollard (use your boat hook) and then take up the slack on the line and wrap around the winch, take out the slack by hand, then pull yourself close to but not tight to the lock wall using the winch. You should be parallel to the wall and able to slightly pivot on the bollard. Use your engine to maintain your position. Reverse will bring the bow out, stern in, forward bow in stern out. Use engine to stay parallel during the lockdown. After locking down, wait until everything in the lock is stable and currents have subsided to unhook from the bollard. Just before unhooking, use the engine in reverse to bring the bow out and then unhook. Proceed out of the lock slowly, gradually increasing your distance from the lock wall.
This technique works very well. My wife handled the line onto the bollard and stayed at the bow with a boat hook just to make sure we didn't have the mast hit the wall. We used large inflatable racing buoys with 55 gallon trash bags as fenders and positioned so that the front of the mast could not hit the wall. Our mast is 50 feet, so we stuck out about 8-10 feet on the front, 5 or so on the stern.
Make sure you have a sharp rigging knife handy in case the bollard gets stuck. It is rare, but happened to us at Stennis lock coming back north, locking up. Unhook from your winch, then get the line off the bollard and just move up the wall and let the current in the lock pin you on the wall. We did and had no damage. you will be going down, so it will be of little concern other than you are not tied to the wall once you get off the bollard. Going down is gentle and easier than going up.
Your second concern will be fuel. When you get on the lake at Guntersville, throttle up to full throttle and then figure out where 75% is and use that for your cruise setting. You will burn about .6 to .75 gallons per hour at 75 to 80% throttle, and should do around 6-6.5 knots, around 7 miles per hour. The river miles are statue miles, not nautical. I'd fill up at Guntersville, then refuel at Grand Harbor and keep track of your hours. That first refueling will give you a per hour flow rate. You can refuel at Clifton, Peeble Isle, Paris Landing, Kenlake coming back, so plenty of fuel stops.
You can likely get to Grand Rivers from Grand Harbor with your fuel on board. Fuel consumption goes up substantially above 75%.
I have a spreadsheet that I used to plan a trip from Lighthouse Landing to Chattanooga, but have not done that yet. It is going the opposite direction but I will be glad to share it with you if you will message me and give me your email. It has mile markers for marinas, anchorages, locks etc. I catalogued information from Active Captain. I used a similar format to Florida and back.
Once back to Grand Rivers think about joining Kentucky Lake Sailing Club. You will get to know a lot of sailors and learn a lot from them.