You're going to get a lot of specific head/cam advice, but maybe take a step back first to what dieseldazzle alluded to in "real 440 car." You want resale value but the prices scared you into looking at later blocks? My opinion is you have to decide which direction first and stick with it. Your time and costs will all be based on that and what you find in the market. The performance in any pro build will be there, but I assume either way in the end it should be a "mild" build on pump gas for your use (not a stroker).
1. Understanding what the real difference is (or is a 440 a 440) (non HP vs HP, and does it make a difference if I do a full build?).
"HP" matters for correct blocks and resale, and performance if it is stock. A "full build" (you mean higher performing top and bottom end/intake/carb/heads/radiator/pumps?) would negate paying higher HP prices. But a "full build" also puts resale in a different category of buyer, one who will pay for performance but not the fact it's an R/T.
2. Should I look for a complete motor or a good block and build from there?
It depends on which route and your patience in finding parts.
- date-correct block ($1000?): stick with stock and a mild cam, resale is key.
- date-correct motor: you'll find Bigfoot before you find this
- 68-71HP longblock ($2500?) or block ($750?): stick with stockish, but most will have been bored.
- 68-71HP motor: maybe ($3500-5000?) that needs work?
- pre-76 non-HP motor ($600?) or block ($200?): gotta go through it anyway, so build for wild. Keeping from 9:5 to around 10:2 for pump gas kinda negates building for wild though.
- 76-79 non-HP motor ($400?): mostly from RVs, have the thicker webbing important to some people when built for racing. No advantage for your use. Ditto work as pre-76.
2a. Is it easy to get everything I need to build from a block?
If you go date-correct , it will be expensive and span a long time sourcing the parts from carb to pan. If not, there are guys who sell turn-key 440s with a pretty good setup for $8-10K.
3. If I buy a complete motor should I expect to still do a complete rebuild?
You'll probably want to visit a machine shop in any scenario. Parts depends on what it comes with.
4. What type of budget should I set, block build budget vs complete motor build budget?
4a. If I build in stages what would I expect, example, 1. purchase cost, 2. machine cost, 3. assembly cost, 4. install cost, etc.
You're probably looking at $6-12K depending on what you start with, staged or not.
5. What's the main difference in heads, 906, 915, aftermarket, etc? (I know the 67's came with 915s, but does it make a big difference?)
915s with the closed chamber would be good for quench, but the price for 1 year only is a premium. By the time you machine the 906s you will be near cost for new aluminum heads that breathe better. But again it depends if you go stock-looking mild or aftermarket high performance.