I was in a similar situation just recently. Hadn't had any urgency (aka not flaring) since last March, and then towards the end of December I started getting urgency. Seemed I was back into full flare mode within a week.
This was my experience - not sure if it will work for you, but hopefully! As soon as I started feeling urgency I started back on the nightly suppositories. One per night, which might be a good bet for you since you don't want to run out before you have insurance again. I also started taking 4 Lialda night again (equiv to 12 Asacol).
I had urgency and cramping for a few weeks, and then D with less urgency, and am just starting to feel like I'm going into remission. All in all it's taken five weeks of nightly suppositories to start feeling normal again.
One thing to note - this was NOTHING compared to the flare I had last year when I didn't take medication as it was coming on. Even though I had urgency this time, with the help of medication it was mostly in the morning. I could leave the house at night without worrying about accidents. I'm sure the Lialda helps, but I feel like the enemas do most of the work.
Good luck to you!