If you make a claim of say $5000 and want to stay insured, do you end up paying it back (and maybe more)?

When I first started glider insurance, I was surprised that you couldn't buy a large-deductible policy. From at least one comment I'm wondering if it's a moot question. I get the feeling that you end up paying in increased premiums for all but the most expensive claims, so maybe it's best to pay for some repairs myself. Any idea where the break-even point is? Will an agent tell me?