Swaps are almost always more work than initially planned for. For all the stuff that has to be disconnected, there are invariably stuck bolts that break, hose connections that won't come loose, other things you discover once you get things apart, etc. If I were you I'd plan it as carefully as I could - but I'd allow a 50% cost contingency (not including the engine - it's likely to cost at least 50% more than you planned for) and I'd allow a 100% contingency on time (it's likely to take twice as long as you planned for). Some people will post and tell you they can pull theirs in 2 hours - that's great. But it's not applicable to your situation.
If you have no mechanical experience at all, it would be really wise to have your partner be someone that's pulled engines in and out before. I had no experience at all with 5.0's, and no experience with pulling them in and out of old Volvo's, but a good bit of experience pulling other engines in and out of cars. It took another experienced buddy and me about 7 hours to get the engine pulled in mine; we were working at a very relaxed pace, intentionally not trying to hurry at all. We pulled the tranny out first from the bottom, exhaust system while we were there, and then proceed to the rest of the disconnects. We labeled every single connection (both sides of each electrical connection) with masking tape and permanent markers - EVERY SINGLE CONNECTION. Don't trust your memory if you haven't done this before. A lot of the hoses, etc. I simply cut as I knew I was gonna put new ones in. If I were you I'd plan for that as well. Doesn't make sense to put old hardware back in with the new engine - especially the radiator - at least have it serviced/reconditioned by a radiator shop. Also, if you're gonna do any kind of engine compartment/engine detailing, now's the time. And that will add considerably to your time.
You may want to talk some more with the folks at Ford Racing about your crate choice with the stock AOD. The ones you're considering I'd only use with an auto if I also had 3.73/4.10 gears and a different (higher) stall speed converter. Those engines are pretty soft on the bottom end (especially the 340HP E cam/345HP B cam versions) and won't be much fun as daily drivers with the stock converter and stock gears.
Things that will help - get some sort of tilt-a-sling to attach to the cherry picker. This will help you alter the angle of the engine/tranny as you're pulling it and putting it back in. Bolt the motor mounts to the chassis, not the engine when you drop it back in. That way you're setting the engine down onto two horizontal surfaces. Trying to get those 2 big studs to both go at 45 degree angles into the crossmember mounts is near impossible. Go to NAPA and get a 40lb bag of absorbent - fluids will get everywhere - the absorbant is a life saver. The main thing you need is patience. Getting in a hurry will cause problems - there's just no way around it. Oh - don't trust the crate engine - check the cam timing, do a compression check while you've still got it on the stand (hook the starter up and turn it over). They're not always perfectly assembled, and you want to know that before you put it in and hook everything up. I've got a buddy who just installed an FRPP crate engine (340HP) and it's looking like the cam timing is 10-12 degrees off. It's easy to check that and fix it if necessary while it's on the stand. It's a total pain after it's in the car.