Seasonal hiring: what is paying well this year? after 13 years as an IT help-desk technician

I am looking at seasonal jobs around Richmond that might lead to something longer. This is my first time dealing with any of this. 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 last year, and it got easier once I kept a simple log of every call and form.