Spinsheet

+1 I was thinking Farr / Mumm 36, but too small.

https://www.fgci.com/products/34/Gelcoat/&Application=Brushable A friend painted his boat with FGCI Brushable Gelcoat 4 or 5 years ago and it still looks great. The cost was under $1k, it took him 4 weekends and he did it in the slip. He found just rolling it worked just as well as roll and tip. A lot of thought needs to go into where you start and finish since you need to keep a wet edge.

+1

You might be able to put a flicker on the backstay, but risk breaking the mast in a gybe. It's a fractional rig, so damaging or breaking off the top section of the mast might be an issue. A genoa and larger kites will give you an improved performance and a known factor at a much lower cost.

HH has a size chart: https://www.hellyhansen.com/en_us/size-chart Have you tried them on yet?

Trump is out of office and now living in your head rent free. Very sad.