Aerodactyl's my favourite Pokemon anyway, but its transportation abilities would make getting the bus or the subway a thing of the past wherever I wanted to go! Although I'd probably attach a cushion or something; can't imagine riding an Aerodactyl to be that comfortable for long stretches of time.
As for the second critter, that's actually a lot harder. My first instinct was to say Milotic, due to its surfing component and general elegance. But I wouldn't be able to go underwater with it, and I've already got Aero that can travel over water... so I'm gonna go with Houndoom. I like dogs in any event, but to have a one that could breath fire would be wonderful protection for anyone that would try and mug me or anything similar like that.
Yeah, that sounds about right: Aerodactyl and Houndoom