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Cheers
It's painful, but worth it in the long run, to save up for 64x boosts before buying much of anything else. The exceptions are spending enough to complete parallel events (they can be done without diamonds but are challenging) and possibly buying the monster girl bundles on a 50% sale (which is an option like once a year).
Characters are another story entirely, however, as many of them are tied to limited-time events that, at this point, come back less than once a year due to how much of a backlog there is of them. If you happen to time your return well with the re-release of some of the earlier LTE girls like I did, though, it can give you a bit of a boost to your progression in the "core" game as well, as the whole "each girl you have at Lover level multiplies the amount of hearts you get for interacting with everyone else" rule includes all the extra characters as well.
The game does reward you pretty heavily in the mid- to late-game for spending a few bucks when you're able, though; two of the best money-making jobs in the game are tied to ownership of the cash-only girls Charlotte and Suzu, respectively (though the new best job is tied to an event girl that will probably continue reappearing around Christmastime). There's not really any pressing need to spend money on gems, though, unless you're impatient and really want to pick up an LTE or Phone Fling character without waiting for their event to return. You'll get a decent trickle of gems over time for free, as I mentioned earlier, by logging in for your dailies and progressing through the levels for each girl for the first time.
Are you sure, phone characters have reruns? I thought I had read somewhere, that only other time-limited characters come back after the initial intro, while phone chars become gem-only.
So make sure to get those daily diamonds
That's a shame. I just started playing the Steam version late last year, so I only have Peanut, Nova, and Lotus. I do wish the Phone Flings were priced closer to the bundles. If they were more in the $2-5 range, I probably would have picked up most of them by now.