I think prepaying by quarter is certainly the better option.

As someone on both side of the rental market (I’m a landlord for a house that I still own, and I rent in a different city), prepaying would make you more attractive as a renter, mainly because it gives the landlord the security, not only that you can afford it, but that you’re not going to leave if you change your mind. But it also puts you at a disadvantage if something goes wrong. Most disputes are not resolved in court because it’s a pain to go through it, so whoever has the money ends up with a huge advantage. I still have two tenants who owe me rent after they broke the lease, and they still haven’t paid.