Traveling race mechanic - health insurance deductible?

I work as a mechanic for several different race teams, traveling to various race tracks.  As an independent contractor who collects Social Security, is on Medicare and has a secondary health insurance/Medigap plan and my own workers' compensation (required by one client), what (if any) health insurance is deductible and where would I list or claim it when filing?

 

Also, sometimes my personal tools are "borrowed" by other mechanics at an event but are not always returned; may I claim tool replacement costs?