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While it is generally good to go with a higher deductible to reap a nice monthly savings, it is not always worthwhile. There certainly is the higher deductible that you need to be aware of (and hopefully saving for), but sometimes the savings is all that significant.
For my auto insurance there are three levels of deductibles: $250, $500, and $1000; I chose the $500 deductible. I saved $45 a month by choosing the $500 deductible over the $250 deductible; this was definitely worth it to me. I called to see how much I would save by switching to the $1000 deductible, and it was a mere $8 per month; that is definitely not worth it to me. So, to save $8 a month, I am in jeopardy of losing an addition $500 until I have done saved the $8 for 62.5 months... no thanks. If I need to save an additional $8 a month that bad, there are plenty of other things I could do, like drop my Internet service to the next slowest speed, pass up two pay-per-view movies, clip more coupons, or do one more mystery shop.
As it happened, it's "sooner."
Other people's prices for different deductibles may work out differently... so you have to look at your own situation and shop around, etc.