I think you're on the right track with the Grandpa's advice, and upgrading to a more capable machine that can utilize your implements better. I've been doing the upgrade thing for years, I started with a 23 HP SCUT w/loader, and while it was a good fit at the time, it was fairly limited in abilities. I could fill the loader with material, and without any rear ballast the rear of the tractor was floating...and pretty limited digging abilities. Now I have a 28 and 32 HP tractor with loaders, and leave the SCUT for mowing/blowing/blading. The 32 HP is a SO much more capable machine.
Only wish I would've started at your age.....!
Take your time with choosing the upgrade, it's half the fun doing the shopping...
good luck and keep us updated....!