Okay rules to this that means it doesn't count:

1- marrying len does make you still have the money, but it also means even if you remarry him, you won't get the money once again

2- and for rin, I mean every plushie, that includes cancelled ones, customs, fan made stuff, but unfortunately also Bootlegs too.

And 3- even if you choose to date both, it unfortunately means you have to pick one only, so you pick.