I also see no advantage. The app that clears the last played list does what you need, should you be worried about it (I'm not, but my ps3 stopped being connected to the internet right before the first time I jailbroke it). I know gaia manager does that cleaning everytime you use it, but there are other options for other managers should you use another.
And to upgrade... I went from 3.41-OFW to 3.55-kmeaw directly without any problems twice, one time with a 40 GB fat and the other with a 120 GB slim ps3 (both PAL). I see no need to install 3.55 OFW in between, but should you prefer to do it, you'll have to use the recovery menu when going from 3.55-OFW to 3.55-CFW if it says 3.55 is already installed when trying to flash the CFW.