I get around the 1 carry on item rule by having my purse/tote bag as an additonal item, but there is no getting around the weight issues on some airlines.

That said, twice I've been forced to put my purse/tote bag into my carry on bag in order to board the airplane.

Once in first class I had the bad luck of being in the bulkhead rule and found no overhead space when I boarded. My SMALL carry on was without a storage spot at all and was gate checked. I was furious! It turned out that passengers in economy had taken up all the available space in first class and the flight attendents did nothing to stop them.

I do not expect this situation to get any more pleasant.