Seasonal jobs that might turn permanent after 3 years as a hotel front-desk agent

I am looking at seasonal jobs around Milwaukee that might lead to something longer. I would like to avoid a gap in my résumé. Is it worth applying to several at once?

Thanks for writing this out. I went through something close to it 6 months ago, and it got easier once I kept a simple log of every call and form.

Keep a list of supervisors' names. A reference from one of them helped me land my next job.