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>Clothes
Pajamas and a bathrobe.
>Items
Eyeglasses, three wristwatches, a cellphone, a small scissor, a camera, a roll of gauze bandage, and as many protein bars I can fit.
>Starter
147: Dratini.
First of all I would try to find some town were I could trade my watches, cellphone and camera for some cash and then buy myself a pair of boots, socks, pants, underwear, a t-shirt, gloves, a backpack, a utility knife, and a flint striker.
I would then pay someone to take me to nearest place that is known to have week wild pokemon roaming around. There I would start training my dratini, feeding him/her whatever pokemon it manages to defeat. At night we would sleep in the wild snuggling together to keep warm.
I would become a dragon-training hobo that travels the world hunting for pseudo-legends.