Trackers are popular and most people love them. They also are not as sturdily built as many other boats (hence that price), so some people that really get on them have issues like cracked welds on transom and transom bracing. Also “bass boat people” are known for being especially hard on boats and engines. You’ll probably get a lot more boat for the money buying used, but if you do buy used make CERTAIN to have a good inspection done. Make sure to look for hull issues and make sure to have a good solid inspection done on the engine—full leakdown test rather than just compression, propshaft runout, check reeds if its a dfi 2-stroke, if it has a computer history check for overheat and other alarms, rpm record (did it spend all hours redlined, or did it spend most hours cruising at 3800rpms), maintenence records, etc. You DO NOT want to blow an engine or get a dog after having just bought it, outboards of any size are not cheap. When you buy a used boat you’re basically buying an engine with a boat attached…so engine is #1 priority, assuming it floats EVERYTHING else is secondary.
Also just depending on what type of boat you and he are used to fishing out of, a bass boat interior layout feels small for the size. Just for example, I think most 17’ walleye-type boats (deep v, shorter front deck, large open cockpit/floorwell, higher sides) feel about the same size as a 18.5-19’ bass boat, even when the hull dimensions are the same. I would encourage you to get the biggest boat you can within reason.
A lot of new boats you’ll spend a LOT on the latest accessories too. Power poles, an ultrex, 12” graphs with side imaging, forward facing sonar, etc. collectively you could just about equal the price of the boat buying new, so if any on this is stuff you want consider buying used and installing yourself.
Pay particular attention to the trailer too. Especially if your dad is going to use this alone and hes getting older, a good drive on trailer is gold. People overlook the trailer, but a crappy one can make it a lot harder for a weaker person to get the boat on and off by themselves especially dealing with wind or current at a ramp.