How do I get my 305 to a 335 stroker, I'm really new to engines, what needs to be done, could I go bigger than a 335 stroker as much as I can do with a 305.

as far as i know you can bore any small block chevy out to a lil over 400 ci. it would be a lot of work, but i assume it can be done

Can I take it to a shop and have them do it? If so how much money does it usally cost?

without sleeving the block there is no way to get anywhere near 400 cubic inches with a 305 block---there is just not enough metal in the cylinder walls---335 is the practical limit---you do it by using the same stroker crankshaft that is used to make a 383 with a 350 block---to my knowledge there is no off the shelf piston for this combination but custom pistons are available-----custom, spelled $$$$$$$-------its cheaper to find a 350 block and build a 383..........................I hope this is useful information for you.........................Dan