Hello everyone!
This trophie seems harder then it actually is! You need to purchase 5 upgrades to your camp! These can be any upgrade! Even the colored flags and outfits. Each flag color cost $50 and with the update to the rewards system this will be even easier to get. Just buy 5 different color flags or actually upgrade your camp which is beneficial down the road!
I have heard that sometimes it actually takes 6 upgrades instead of 5 due to a bug so maybe try an extra color just to be sure.
Hope this helps.