I have alot of weight to lose. But I know that measuring my inches is also a good measure of progress. How often should I measure? Once a month, once every two weeks?

I would do it every month or so, shortly after your period. That's when you're least likely to be retaining water.

More often than that, and you might be disappointed if nothing changes, or if the numbers have gone up.

I'm starting to measure at every 5 lb loss and will take pictures in a bikini at the same time

Then I'm posting them for the whole world to see cause I'm crazy.

But...the last set of pics is going to be so amazingly awesome that the embarrassement will have been worth it.