Eh, there is pertty much 1 thing that determines how well you do in this "tournament":

How upgraded your decorations are/which ones you have.

Generally speaking, you're gonna plateau after a couple hours. So starting late isn't really *that* big a deal. (particularly since rank doesn't matter).

It also, of course, means at the beginning you're going to be shooting up through the ranks until you pass everybody who has a lower "plateau" than you. Then you'll just fluctuate around those with the same plateau based on whose currently "active" and is squeezing in a handful of additional levels here and there.

That said, I expect any expensive girl other than Judy is just lowering your plateau. They don't increase your income *that* much, and they're just keeping you from getting a whole bunch of cheap levels.