I've got a vortec 350 that needs a new crank, so I'm gonna stroke it to a 383. The entire engine needs to be redone. I've never rebuilt an engine before. Since I want to get it done right should I take it to a machine shop and have them do it, or do you think it would be easy enough for me to do myself. Also anyone got any idea of how much a machine shop would charge?

 

My opinion: take it to a machine shop.

we're talking about clearances as close as .010 inches. no room for a slight mistake by a first timer.
If you think you want to learn how, then get someone's 305 they are throwing away and play around with that.

 

If you're careful, take your time and have all the right tools (plus some... ) then you'll be fine. Just buy a couple good engine rebuilding books. I reccomend Building the SBC by SA or something like that, can't exactly remember. Just make sure you triple check everything, and if you still think it's wrong check it again. If you have any problems you can always ask here. There's a first time for everything, and personally I take pride in building my own engine.
For a 383 you should do a search for details on parts you need, but I'll give you a short list: cast stroker crank (preferably internally balanced), new pistons, rods will need reconditioned, clearancing on the block and possibly rods, and small base circle cam. This is just the basics, do a search and you'll find out everything you ever wanted to know about a 383 plus some.
Like I said if you have any questions don't be afraid to post up here, and feel free to pm me if you need anything. I can probably answer most your questions and if not I know someone who can.

BTW, .010 is a big clearance in an engine, you'll be dealing with much smaller (sometimes .005 or lower) so a set of feeler gauges, micrometers and calipers are recommended.

 

For a 383 you have to let a machine shop bore it .030, you cant do that at home. Plus depending the route you go you'll have to balance the assembly, another thing you cant do at home. You can relieve the area on the block at home where the rods will hit the bottom of the bore.