Virginia hunting?

Don't over think. Any gun will do as long as it falls within local hunting laws, and you can hit what you're shooting at with it.

Why do you need a tree stand?

I'm OCD about odor. That's a deer's best defense. I've stood out in the open during hunting season and had bucks walk right by. I've seen them try to pick up my scent when I've been standing in the open, to no avail. I would not suggest using any bug repellents.

Clothes get washed in regular, inexpensive, free and clear detergent. I wash body and hair with hunting specific soap, and spray everything not kept inside my pack. The stuff I have right now is Dead Down Wind.

Deer don't have good vision, but they can detect quick movement. I like to stand where I can see and shoot 360 degrees. I just make like a tree. You can lean up against a tree and disappear. My head is on a slow swivel. When I get bored or tired of standing I'll walk very slowly. Scout Sniper slow. If a deer jumps I'll freeze and wait for it to return. After 20min or so I'll start walking again, if it doesn't return.

A tree stand would be more comfortable, and that's part of the problem. I'd be asleep in no time. I fear the same if sitting in a ground blind, even though I own one. Have yet to use it.

That's what I've come up with for hunting in my AO. I assume you've been doing some research on hunting websites. You might find good info specific to your region.

Woods or fields? I'd prefer the 1-6 in the woods if there might be close-range shots, and 6x is still sufficient for fields.

One thing I would suggest,depending on your weather,is appropriate clothes,boots,for the weather.If its cold and you are sitting still,be sure to buy the best insulated boots and clothes that you can afford.

Nothing worse than freezing sitting still in a stand.

You can't overdo scent control IMO. Playing the wind is really important.  Dress so that you're not freezing and can sit still.

Maybe try a cheap ladder stand to start out?  (I haven't bought a stand in a while so I'm not sure if they're actually cheaper than a climber).

Not much else you need really. Rifle setup will depend on your AO.

I butcher my own deer and hogs using a home depot box cutter with carpet hook blades (hey it was like $3 and works great), an esee 3, and a boning knife. If you haven't butchered anything you can find 1000s of youtube videos.  It's really not too hard and I think it's rewarding.

Don't forget the safety harness when using a tree stand.  Have some rope or para chord.  You will only one good sharp knife to gut and quarter.

As far as the rifle, .300 win mag will work fine with the 1-6 scope.  I have a .300 win mag with a 6.5-20 when I hunt with it I use 200gr Nosler Accubonds.  Most of the time I use a RRA .308 with a 3-9 scope and 150gr Hornady SSTs.

Use some kind of scent killer body wash and laundry detergent, plus a field spray for when you get out of the truck. I personally haven't had any issues with being scented after treating my clothes with permitherin and I have to get alot closer than you. With the ticks being as a bad as they are around here, if the deer noticed it, I'd use it anyway and mind the wind. Make sure you have warm enough clothes and boots especially if you are going to sit in a stand or blind all day, it really sucks to have to call it a day early because you're frozen to the bone. Depending on the area you'll be hunting you might want a cart or cheap toboggan to drag it out, it's a pain in the ass to drag them through thick brush without one.

Check out this article from Realtree: How To Deer Hunt.

I would recommend an optic, as it will make low light shots much easier and deer like to move early in the day and late in the day when you may be dealing with low light.

Either rifle will work, but I would go with a 1-6 optic over the other high magnification choice. I typically use a 3-9 or 2.5-10, but they stay on the lowest power most of the time. I rarely use the higher end. It's just there in case I need it. I've never hunted with a .300 Win Mag, so I don't know which projectiles would be best. Don't overthink it though. Winchester PowerPoints or Remington Corelokts have been killing deer for years. They're not the best at everything, but they work.

Scent control is the number one factor. If you use a climber, you can get higher which helps some. I typically hunt at 30'. Some people say anything over 20' is excessive, but I like being up there. I've had deer walk directly downwind of me and never smell me up that high. Get a good harness that is comfortable and easy to use so that you'll wear it. I like the Summit stands. I rifle hunt from a Viper and bow hunt from a Razor. Another benefit with a climber is the flexibility. If you set it up one day and see that you need to move, all you need is a suitable tree where you want to be for next time.

As for clothes, learn to layer intelligently. This is especially important with a climber. You will get hot while climbing. If you dress to stay comfortable while climbing, you'll freeze when sitting still. If you dress for sitting still, you'll get hot while climbing. Figure out the layers you need and learn to put them on/take them off in the stand. On the coldest days, I typically wear a polypro layer, a fleece layer, and a wool layer on the outside.

Hunter Safety System is probably the easiest to use and a lifeline is just as important, I've had a few close calls getting out of the stand because my hands and feet were numb and won't go without now.

What you really need is as follows:

A rifle and ammo.  It doesnt need to be a magnum, and it doenst need to be premium ammo.
A license/tag. and something to affix said tag to recently deceased deer.  I like zip ties.
A knife to field dress your animal.  While not necessary, some packaged jandiwipes can be nice for cleaning gore off hands.
Some decent warm clothes and a decent pair of boots.
Either a small closed cell foam pad, a small folding chair, or an old milk crate.
A decent headband mounted Petzel type flashlight.

That is it.  tree stands, cammo, cover scents and all the rest of it are not necessary.  Ive killed far more deer just walking slowly and quietly or sitting on a milk crate or old five gallon bucket than I have in a stand or blind.  If you keep working into the wind, and keep movement to an absolute minimum, you don't need cover scents and camo.  Deer see movement REALLY well.  But they don't really zero in on color all that much.  

I;ve repeatedly had deer walk within 20 feet of me, as I stood on the ground or sat on a stump.  If they were up wind (thats planning, not cover scents), and I didn't move, they did not clue in.  And with the right weather (moderately gusty, so leaf rustle covered my noise) I've stalked within 20 feet of bedded does, and they've never known I was there.

Technique works better than gear collection.  Better to spend lots of time scouting, patterning, and understanding your deer movements than to buy tons of junk.  If you KNOW your deer patterns -  where they bed, when they move to feeding areas and how they get there, what the predominant winds are, and what natural ground cover exists, your deer are pretty much already in the freezer.  they just don't know it yet.

go walk the woods.  Find them.  Watch them.  Understand their movements.  A little knowledge is worth more than a $1000 worth of camo, optics and coverscents.  Once you have them figured out, a 30 yard chip shot with a walmart sourced 150 grain soft point out of a $200 garage sale Winchester 30-30 will flatten them reliably.

Ammo:  In my experience, 308 isn't a 'fast' caliber.  A 150 will open harder and faster than a 180, but will still totally exit.  a faster expander works very well in 308.  Nosler partition, hornady SST are great.  Regular old school winchster powerpoint and remington corelokt will work very very well.  Premium bullets like barnes X and the other deep penetrators actually are LESS effective than the rounds noted above....  they do a lot of their expanding and killing in the hillside behind the buck..

In the 300 mag, the ballistic tip and the SST are NOT recommended.  Subtantially higher speeds will over stress these bullets.  A harder, more controlled expander may be a good idea to limit over expansion at magnum speeds.  

Personally, a 308 with a low lower scope is about as ideal a deer rifle as you can get.  Onwards of 25 years with a 20" Remington model Seven in 308 with a Leupold VX-III in 1.75-6x has accounted for a couple dozen freezers full of venison.  I use a hand loaded 165 Nolser ballistic tip at modest speeds.  Ive tried over bullets but keep coming back to these.  I would not even think of using these in something fast (like my 280 Ackley) but they are nearly 'perfect' at the modest impact speeds of my Seven at the usual 20-175 yards I shoot,

Fro

Fro

Where in Va?

Find a friend to go with.  Someone with experience.

I remember shooting my first deer, the guy I was with is still my best friend, and we have killed a lot of deer together.  But when we saw the doe I remember asking him "what do I do? ".  He told me to "fucking shoot it!".  That seems dumb, but having someone else as a coach made a big difference.  And I really had no idea what to do after I shot it - having someone help you with field dressing (gutting) that first time will be huge.

We are going on our biggest, longest hunt ever in the spring - South Africa...

I used an HSS harness for years and they are a good choice. I use a Summit harness now, but I wouldn't say it's any better than the HSS.

I forgot to mention the lifeline. Most falls happen on the way up or the way down. USE A LIFELINE! I clip in as soon as my feet leave the ground and stay that way until I step off the stand.

I'd recommend a Black Diamond Alpine Bod harness.  I used a reversible HSS vest for years and didn't like the weight, the heat, or having to try to slip out of it to add or remove upper body clothing layers.  The climbing harness solved both of those problems handily.