elkhunter, don't worry about the "dumb" questions, there aren't any. We have all been there and had someone help out, so we return the favor.
First off, you have to decide what is LR to you, 300yds, 500yds, 1000yds? Makes a big difference. With a 338 Win mag and bullets like the 225gr BT, 250gr MK/Lapua, you are going to be able to deliver a heavy blow way out there. I would hazard 700 to 800yds if your rifle is accurate enough.
The drop doesn't matter as we dial up our scopes for all ranges. Dialing up a few more clicks won't matter. As long as impact vel is over 1400fps, you are going to put a big hurt on whatever gets in the way.
The big issue is how well does this rifle and you shoot. You must have equipment that can hit a gallon milk jug everytime at the longest distance you want to shoot. For some of the gear on this board, that is in another time zone. After having had a chance to shoot and work up your loads, you will know if you need another rifle/barrel or not. If you like the cal, shoot what you have first. Can't see why it wouldn't make it to 400yds at least - that is a long ways to start.
For scopes, the best bang for the buck is the Bushnell Elite 3200 10X. A very nice scope with enough elevation to make LR hits possible. If you have more coin, then Leupolds, 4200Elites, Nikons, Tasco super snipers, etc are all possible. Again, you need to know how far you want to go and how much elevation you need to make the trip. Most 1" scopes have 50min of elevation which can get you out a very long ways (tapered bases and Burris Sig rings will shim scope to account for a "high" 100yd zero).
Magnification is up to you but I find the 10/12X to be great for ranges up to 700yds.
The big part is the support equipment. You must have a laser rangefinder, good binos and spotting scope. I would suggest the Leica 800's which are going for cheap right now. Binos/spotting scopes are going to cost but without them, you will not be able to see game to shoot at. I just bought a Nikon Monarch 8X42 binos and am very impressed. Affordable, waterproof, and I will find out just how good the optics are (going hunting this week). Pentax also makes very good optics for the money.
The final equation is practise, practise, practise. You must shoot to learn about ranging, and wind doping. If money is really an issue, then consider an accurate 22LR and shoot at 200yds. Believe me, that if you are not holding or doping well, you are going to miss in a big way. Most 22LR will shoot 2MOA or under with decent ammo. Practise on tin cans at 200yds and you will learn lots and impress your friends. When that gets boring, go out to 300yds.
What you learn with the 22 will transfer over to the big bores. it is not a waste of time. practise as much as you can with your hunting rifle from field positions and distances. This confirms your drop tables and you learn how to shoot without a bench.
Over time your confidence and distance will increase. enjoy the journey...
Jerry