I've got a good grasp on skin retouching but I still have
problem retouching hair, more so massive strays over
skin like the neck. I'm stuck with editing image from my
set because I can't get past this portion of editing.

How would you guy edit the hair on the neck and still
have a natural looking hair/skin edge?

first, clean all that you want with frecuency split and D&B and then paint with a small brush like three or two pixels at 80% to make more real the retouch.

I've done this before to a somewhat lesser degree and here's what I did.

1.Healing brush/clone/patch away all the hairs, sometimes it helps to do this on a layer sent to lighten first then again on a normal layer.  I didn't really worry to much it it looked all messy and gross because after this you...
2. D&B the heck outta the parts you fixed because I honestly feel like there's no simple&good&fast way to get ridda those hairs you really have to spend a lotta time healing then D&B
3. (optional)Draw in some new hairs near the edges to help keep it looking real, do this with the clone tool and a very tiny brush with the opacity set down a bit.

Sometimes though if I'm in a rush I'll create a surface blur layer (I know, blur ahhh!) and set it to lighten or normal if perfection isn't a big deal with the part that need to be fixed masked.  You still have to do the other two steps it just makes it go a little quicker.

All that being said, if all the hair is messy like that, sometimes having a nice smooth cut off looks weird, so make sure all the rest of your hair is nice and tamed after you do this!

Here's an example from my port:

Use the clone stamp tool with 40-70%hardness, 100% opacity.

In this case I probably would split frequencies - on high over messy hair I would clone good neck texture and then clone/paint in on low layer or blank layer between good neck color. (both probably with pretty large hard brushes)
I would do it in larger area than needed. After it's replaced I would make Inverted mask to all frequency separation group and paint in where I need it. After that D&B to fix or change any problem areas.

On a blank layer, I would clone out all the frizzies with a large brush, going well into the good hair, at 100% opacity. Put a mask on that, define the hair edge fairly sharply, then on a new layer sketch in some hairs to break up that line so it makes a natural transition to skin.

Peano +1

+111111 Peano for going beyond and showing the result.

Ken Fournelle wrote:
Peano +1

Thanks for the many responses, I'll give them a try.

how to draw the hair and having it looking like real hair?

With Peano's approach it is often necessary to apply noise and blur to the added hair to blend it in.

Approach I use is variety of a couple of ways. First I would clone in a peace of skin to cover that area(if delicate clean up doesn't work). Then I would reveal the hair strings that can blend in with the hair I draw. I also look for the hair peaces around in the image or if possible from the other image and clone on top. It is a play around approach. I can end up with group of layers consisting of quiet a few layers. Once the  appearance look natural a leave it to dodge and burn, color adjustments , contrast and etc.  I was hating the idea at the start that I will have to learn draw the hair but once I managed to do it's very helpful. Having said that I get  angry when hair stylist doesn't do a proper job. Photographer should also pay attention to details like that.

+1

AKMac wrote:
With Peano's approach it is often necessary to apply noise and blur to the added hair to blend it in.

Thanks Peano, great advice....