I paid $A500 for a 30 day trip last year and have opted for cheaper insurance with the same coverage this year for $350 (which included removing the excess). $500 Australian for a month is a lot of money. I am 70 so no insurance is not an option. The cheaper policy will almost certainly not be as easy to claim on, but the policy I had last year is now $570, and I am not prepared to pay so much again.
Travel insurance is becoming as costly as air travel. Probably a necessary evil but I can understand why people travelling for long periods are reluctant to pay the high premiums.
If you are changing $1000, an extra 50 satang adds up to 500 baht, which may not warrant going all over town, but would certainly cause me to seek out the exchange place if within a reasonable distance and cost.