i've found the best way to upgrade gear is budget $1500 a year.
that gets either a board or 2 sails.
just rotate the purchases,
1st year, 2 sails
2nd year, board
3rd year, 2 sails
4th year, board
that way all gear is between new and 4 years old.
fins are xmas/birthday presents.

masts and booms last ages if the right ones are bought so over the time they don't cost too much.
bloody hell it's hot here right now. calm before the storm.