magento - collect extra data during account setup

hello - i have a new magento shop that sells dog collars, clothes and leads. i want a function for the customer to input information about their dog or dogs.... the idea is that they enter the dogs name, birthday, breed and size measurements (4 measurements of neck, ribs, back and stomach. the customer then has to select the dog(s) name for each order line(s). this will help us to see customers that order the wrong size items and we will collect DATA in a table that can be used for marketing specific to large dogs or small dogs or specific breeds. 1 allow the customer to create and remove an unlimited number of dogs on their account during setup or after setup 2 select the dogs name from a dropdown for each order line during checkout 3 send a pre-set message to the customers email 1 month before the dogs birthday .....also i think it might be a good time to upgrade from current Magento ver. 1.5.1.0 so allow some time for this and any related problems. an ideal scenario would be for the automatic recognition of product size miss matches. if the customer adds an item to the cart but the size attribute does not match the size of the dog (customer creates a dog called "buster" and enters collar as 35cm but then adds a 20cm collar to the basket and select "buster" in the order item line). this is not important but if achievable and affordable we would consider the extra work.