Under eye treatment helps, but they do not perform miracles.
As far as your hair, im not too sure what you mean by poofy. If you mean frizzy, get a good deep conditioner. Frizzy hair is caused by overly porous hair taking in moisture, making the hair swell. A good deep conditioner can do wonders. Make sure you wet your hair with warm to hot water, and rinse with cool water. When you towel dry, hold the towel to your hair, do not rub your hair with the towel as most towels are more course than the strand itsself and it may cause damage to the cuticle layer (the layer responsible for porousity). A few trreatments can do wonders.
Picking a good stylist is tough. Do not go to a barber as they normally do mens cuts, and are more acclimated with mens styles and arent as experienced as a cosmetologist is at cutting womens hair and styling. Many though, will want to cut your hair short because its quicker and easier to do. Cosmetologists do not care what gender theyre servicing, as a matter of fact many will be excited to try new things with you.
Im not too sure how painful waxing is pre hrt, but about 5 months into hrt thre was very little pain when waxing. This is just my experience however.
A thicker neck does generally make a face seem more masculine.