Sell my 2nd gen for 3rd gen?

Hold out for a 4th Gen, and make everyone jealous of you....

 

I had a 2007 and upgraded to the 2019. It wasn't as much of an upgrade that I hoped. Way more comfortable but less fun. If you're cool with the 2WD stick with it until it dies. Save your money.

 

Rotor issue do the upgrade.

paint you can vinyl wrap or repaint. Even in Durabak bedliner type coatings in smooth finish for a cool color not otherwise offered.
Toyota probably still paints the same way.
Or polish wax and ignore it.

addressing the paint may even be cheaper. You can convert to 4x4 or sell and get an old 4x4.

 

One would have a hole in their skull to pay todays interest rates on a new vehicle.
Unless you can afford the cost I would make do with what i had.