oldhammy1,
You sound a lot like myself, interested in putting the best you can into what your doing. Here in my part of Texas, I have grown up hunting in many different surroundings. When I was just starting out at 6yrs old we hunted over corn feeders in the hill country where more than 20 deer would pile in when they went off. For me it was a learning experience in how to shoot one, not so much of how to bait one in. The ranch we hunted had to take so many of the does off each year to sustain a population that wouldn't over run the natural vegitation.
As I grew I hunted hardwood forest, swamp bottoms and river bottoms as well. No feeders but an occaisional food plot. The plots were there to add to the deers overal minerals and as additional food for them and were not generally hunted over.
Bringing my grandson into hunting I set up a feeder to enable him to have not only a more stable shot on the animal but also to allow him to see more game while out. We have only taken feral hogs under the feeder so far and he is two for two on that. Being he just turned 6 this past Thanksgiving I figure he isn't doing to bad. He also scored a yote out just over 150yds as well. He uses a Ruger Compact in .308 with reduced load put together by me. A couple of weeks back I upped the dosage on the loads and brought him up from a 125gr bullet @ 2200fps to a 130gr bullets @ 2570fps. This will help him to reach out a little more efficiently on a couple of deer we have had to pass on due to the load he was shooting.
In your case, if I were looking to do what your looking into I would take a good look at the Barnes TSX, they are a bit pricey but the preformance I have gotten and heard reported from other reliable sources has been wonderful. THe Accubond or Interbond are also great as well. The thing with the TSX is that you can drive them to a tad higher velocity per weight than normally constructed bullets, and the recoil isn't as amplified. This was one of the considerations I had to deal with on the little Ruger for the grandson, since the rifle only weighs 6.5 pounds field ready, and the kid is only about 65 pounds.
I know you mentioned wanting a 300 Win mag, but also consider using the newer 300 WSSM or the 300 RUM as well. With either you do not have to deal with the belted case. Both will drive anything from 165 - 200grs easily to velocities you will need for extended range shooting. One thing on the RUM is that Remington also loads three different power level factory loads for it as well. One is close to '06 velocities, the second is a middle ground around the .300 Win and the last is their top end loads which are pretty awesome. As for recoil yes the RUM has it and if your not against a brake, they make this a very tame critter. I would suggest looking up Definsive Edge and getting in touch with Shawn Carlock. He has built a brake which is very well adapted to these type rifles and his work is outstanding. I have personally shot a RUM with up to 240gr bullets ripping out at max velocities and the recoil is light enough to see your impacts at 500yds through a 15x Nightforce.
I also understand your way of thinking on the close verses long shots. Most of my hunting is in river bottoms but I also hunt our family farm. In the bottoms we might get 100yds if yoiu thread the needle, on our farm your looking across flat hay fields whick if the deer is at 450yds well thats as close as your gonna get ot him unless he walks your way, which don't happen very often. I am an accomplished shot out to 500yds easily with several of my rifles in varoius conditions. my longest shot on a whit4etail was just over 400 yds using my 25-06 and a 115gr Partition. I know this load and rifle inside and out and it was not a problem to hit exactly where I was aiming under the conditions I shot in. The deer was standing perfectly still relaxed and eating, the sun was illuminating him and everything around him, the wind was non existant, and after the break of the trigger I recovered the sight picture just as the bullet impacted right in front of his left shoulder dumping him on the spot. Could I have gotten closer, possibly had there not been two dozen or more deer in the field. However in some situations there isn't that choice, and if you shoot your rifles at ranges way beyond what you ever ecpect to shoot, then every once in a while, you don't have to watch that buck of a lifetime walk out of sight due to you not being sure of yourself.
I wish you all the luck in your endeaver and hope that which ever you choose it is a shooter for you.