chrominance
Member
You don't always need to wait for a text. When you have free time, hit the map; when you press Square, each location will show you who (if anyone) is available that day. Ann always hangs out in Shibuya's underground mall, so just highlight Shibuya in the map, hit Square, and see if Ann's name shows up.
This is assuming that you're literally at rank 1 with Ann (as in, you've already seen her first confidant event); if you actually mean that you haven't started her confidant stuff at all, then be aware that you'll need your kindness stat at level 2 to start her storyline.
Mementos is your friend. Abuse it when you can. Even if you don't use any exploits or tricks, you can make plenty of cash just getting as far into Mementos as you can every time you go down there. The Fortune confidant has an early ability that increases the amount of money you make that day, and the Sun confidant has shadow negotiation abilities that let you knock down shadows and then, instead of an all-out attack, allow you to milk them for money instead. There's also all the treasures you can sell, and if you go into Mementos on a rainy day, there are additional treasures and treasure shadows that are worth lots of XP/money.
And then, if you DO want to go nuts, there's always the confuse trick. In my NG+ playthrough I'm sitting on a cool 3.3 million yen.
