There's some calculators out there that can give you a rough estimate. I usually us 7200 RPM as the max RPM of the bike - it can go higher, I just don't usually do that.
14/39 with the OEM tires is around 57 mph at 7200 RPM (GPS, not indicated speed, indicated speed will be higher). I think we've already determined in multiple posts on the forum that you're using a downhill, drafting or a very strong tailwind to get that speed. Bike doesn't really have the horsepower without a BBK to get to that speed easily.
14/45 with the OEM tires at the same RPM is ~49 mph. It will definitely hit that speed. 1st will be very short, but the gap between 1st and 2nd will be a lot smaller.
13/45 with the OEM tires at the same RPM is ~45.4 mph.
At 280 lb I'd suggest buying to the JTF 273.13 13 tooth countersprocket first with the OEM chain and rear sprocket, and seeing how you feel about that. It's an easier install, cheaper, and will give you a good idea of how the gearing will make a difference. If you like that, then start with the JTR 269.42 combined with the OEM 14t countersprocket and make smaller adjustments to the rear sprocket tooth count - for example, I like the stock gearing, but I'd rather have a 40T rear sprocket. If you feel it still doesn't have enough OOMPH even with the 13T and you never see the top speed of the bike, you can try the JTR 269.45 rear sprocket + OEM countersprocket and see if that makes a difference. That being said, power is energy over time, and energy is defined as the displacement of mass by force over a distance. The bike is 9hp, there is no gearing that refutes the laws of physics of heavy rider + low horsepower = slow up hills. The main difference is you might have access to a different part of the rev range of the bike, which might help a tiny bit, or put you at a different speed on certain hills where the gear you'd normally be in forces you to either speed up or slow down.