Seasonal jobs that might turn permanent - what worked for you?

I am looking at seasonal jobs around Minneapolis that might lead to something longer. There are 7 people counting on me, so I am trying to be careful. I would like to avoid a gap in my résumé. Is it worth applying to several at once?

Keep everything in writing and save the confirmation numbers. It saved me later.

Apply to several. Start dates and schedules change quickly and having options helps.