@Daniele **********
don't try to live here on those 60 day visa excempt entries. You will get stopped and denied entry sooner or later. Likely sooner as it is. You are cutting it short with the time for you applying vs expiration of your current stamp. Let that be a lesson for next time. It's wise to apply as early as possible. You would not lose any days, and it gives you time to correct anything that might be a problem with your application. Believe me, using the same office for 8 years straight now, for marriage extension, the exact paperwork they want each year can be slightly different. Let yourself have a buffer for that by going early and not having to stress about it.
For now though, worst case? Lets say there's something not okay with your documents, and they ask for additional/changed/updated something, and your time is up.
Then there is the 60 day visit family extension, that you can use only one time per entry. It has more or less the same requirements as the one year extension, just minus the money.