I recommend not "investing" in a city-state unless you can get some influence for free to start out. Killing Barbarians or doing another quest for them will get your foot in the door, and let the $250 you have to spend periodically give you a lot more value. For instance, that $250 will be keeping you above the "Allied" line instead of just barely making you friends with the city-state.
Likewise, as mentioned above, the Patronage tree will give you significant bonuses to your influence over city-states.
It seems that the design is such that in the early game you won't be able to guarantee a city-state ally without committing a lot of cash.
To elaborate (not 100% sure on all these numbers but the overall point is still valid):
If you spend $250 to become Friends with a city-state, starting from 0 influence, you'll get 35 influence, making you barely Friends (30 influence). This means you'll be friends for 5 turns, at which point you'll need to spend another $250 to be friends again. You probably don't have another $250 that soon, though, so the influence runs all the way down close to zero before you're able to spend another $250, which again only gives you a few turns of friendship. This is obviously unsustainable.
If instead you perform a mission for the city-state and get 30 or 40 influence to start with, every time you spend $250 you'll get to use all 35 points of that influence before needing to spend another $250.
Similarly, you'd be better off saving your money to start with $500 worth of influence than buying $250 and not being able to afford more right away.
Long story short: if you're already friends, you get more value for your money. Likewise, if you're already allies, you get even MORE value for money you spend to sustain at that level.