Hi. No my insurance didn't cover it, I chose to pay privately. It cost £150 + £25 for the painkillers / antibiotics. I guess thats pretty similar to what you have been quoted in $. But we've not had the additional expenditure you have had, so it was not such a difficult decision for us.
We are very lucky in the UK in that we can can fertility treatment free of charge, but there are long waiting lists, so DH and I decided we wanted to get the ball rolling, particularly as I have PCOS and it will probably take me me longer to conceive anyway.
My doctor advised that people should have the HSG from day 1-10 of your cycle to ensure they are not performing the HSG when you could possibly be pregnant. If you have a short cycle they may suggest different dates.
I am sure you will be fine - it really is quick (10 mins), so the discomfort is just for a short time.
I was lucky - i was given the all clear and am starting clomid next week. Fingers crossed for you.