Complete newbie, feeling out first project

Lets start with the amount of experience I have building/working on pushrod engines: zero. I've been absorbing all the knowledge I can across the web, and looking the start my first project in the next few months, and have a few questions.
I'm looking to put together a 450-500 hp foxbody with a 460, mild build, street only. I currently have nothing for it. My total budget, including the transmission, rear end, chassis, and everything I need to make it go is 20k.
Firstly, I'm wondering how practical building vs buying is. A small part of the reason I want to embark on my project is the learning experience of building, but having no practical knowledgebase and no friends/family to pull from, I'm wondering if having someone build the engine for me might be a better path.
Second, if I choose to build, given my lack of experience, I was thinking about using all new parts, including the block, just to eliminate as many potential issues as possible. Is this completely insane given my intended use and budget? I realize this will cost me a decent amount of money, but my goal is to build a bulletproof car, overbuilding is a plus, since I wont be the only common driver, and I'm hoping to not run into things breaking because I skimped in places; a reliable daily driver. It seems like all the build guides for the level of car I want to build, and even most of the crates that are fairly similar to what I'm trying to do use a stock block/heads/crank, with some machine work.

Talk to Bob at D&D in Lebanon PA for a complete swap kit.

460 with a C6 and a worked over 8.8 will be the ticket.

First thing to do is buy this book:  

http://www.amazon.com/How-Rebuild-Ford-V-8-Engines/dp/0895860368/ref=sr_1_1?s=automotive&ie=UTF8&qid=1436629408&sr=8-1&keywords=how++to+rebuild+your+ford+v8


Read it from cover to cover before you do anything else.

A lot of this should depend on how mechanical minded you are.Do you have any tools to start out with,such as the ones necessary to assemble the engine.Then you will need a engine lift in which you could rent or borrow. We can help you w/necessary knowledge to perform the task in hand. It brings great self satisfaction to say you built it yourself but sometimes starting out it is a lot less costly and a lot less hassle to buy a similar build to your liking,and get the feel of working on it and go from there. But you have came to the right place for help.We will help as much as possible.

For 20k budget you would be much further ahead buying a built car. You will still have plenty of work to do to get your hands on experience.

New nlock would be insane for quest.  You have the same 2500 in machine work for a virgin green block as you do a seasoned pick and pull.  FRPP still sells 514cu in stroker 460.  If you want a plug and play.  Virgin FRPP or basic dart etc, unless your buying from a company thats selling it machined and assembly ready..
 Has to have finish machine work done.

Depends on what is done, align hone mains, align hone cam bore, size lifter bores, bore hone block, sonic test before any machine work, etc..
All required for 500? No, Could probably get away with simple check for cracks, bore, hone, wash and go.........

All required on virgin green block, yes. Unless sold otherwise, and cost would reflect it.

And I was wrong, FRPP no longer offers the 385 series engine. They have a 427 cu in small block at 575hp, but everything is now on Windsor/boss block.

I think its very doable. you picked the right chassis as everything you need is bolt on , no custom fabrication required. With that said you're first project will be a big one and at some point you will feel overwhelmed. My best advise is start with a running car begin with the small projects first, (replacing suspension pieces, preparing rear axle, updated brakes, new fuel system etc. ) before you get to the engine swap. the longer you can keep it running the less likely you are to get overwhelmed and lose interest in the project. Ask me how I know. My first big project ended up on a rotisserie after I had a master cylinder go out. We often learn more from our mistakes than from our successes....the down side of that in this hobby is that your mistakes are usually fairly expensive

bill