Question no.1 I think it just gets easier with practice, the items you eat most often stay high on the list - as for the ounces and that if you think you are not good at guestimating why not get a small kitchen scale they are available in a wide price range in stores like wallmart and some pharmacies - maybe even some grocery stores.

As for question no. 2 I can't really help out I don't keep a journal at fitday so I've never tried to make a link to it - but I'm sure it won't be long before someone answers that for you.