Square Jaw Photography wrote:
I feel my photography is at a level where I can start making money off it, and I want to enhance my best work to a level that is on par with most of the high-end ports on this forum.

retouch work, generally, will not translate into boosting one's level up. "generally" is broad. this isn't the critique forum. let's just say you have a rather high expectation for the retoucher.

first you have to understand your market. will the money spent be recovered or will it increase the worth of the images to be worth the cost? will the client see the difference?

yes, except for e-commerce, product catalog type shots, pay by the image type work isn't usually the type of pay needed for great retouch. but then $20 per hour is not "high". in fact it is quite low as far a good retouch work goes in the usa. so if you spend $100-$200 to retouch an image, what is the gross profit you must make for that cost to be worth while? what client would pay that cost and how do you get those clients?

Are my photos worth paying for retouching?

Every car is worth washing. One either washes it oneself or pays another to do it. Meanwhile one can do something else (e.g. shoot another model)

How would you state specifics for the retoucher, without truly knowing what your images need to really make them great? Where can I go to learn all these?

The point is not to send to the retoucher something vague like "I want basic retouching" or "I want superb high end magic" and then wait with crossed fingers for a disaster to strike. A proper requirement would rather be definitive and descriptive: "I want clean up of studio floor, remove stray hair on model's cheek, change lipstick color to ..., remove tattoo on left arm, color grade like this example+link(s)" etc. Then the requirements are actual objectives which can be followed and evaluated.

Square Jaw Photography wrote:
... I want to enhance my best work to a level that is on par with most of the high-end ports on this forum...

You need to ask for advice from photographers whom you respect, not internet strangers.  You may need to pay them.

Square Jaw Photography wrote:
... How would you state specifics for the retoucher, without truly knowing what your images need to really make them great?

You can't. Ask for advice from photographers or retouchers whom you respect.

j francis photography wrote:
It's not a lifetime commitment. Pick someone you like and give it a try. The worst that can happen you are out a little money and you learn something.

That's essentially what just happened. I provided clear instructions on what I wanted done, but in the end, I was disappointed. I want to know my photos will come out good when I invest that kind of money.

Mark Salo wrote:
You need to ask for advice from photographers whom you respect, not internet strangers.  You may need to pay them.

This implies that everyone here is an internet stranger who deserves no respect whatsoever and one should surrender oneself to people who stand on a pedestal and take one's money for giving advice. Obviously that is not so because both Leonard and Steven have given valid answers.

You can't. Ask for advice from photographers or retouchers whom you respect.

Of course he can. I already explained how simple it is. There is no need to ask Mario Testino whether you want that lipstick color changed.

Retouching itself cannot improve the essence of the image. If it is used for that purpose it is definitely a sign that there is something quite wrong in the previous steps of the photographic process. What makes an image great is what it displays, not how it is retouched. This means good pre-production (casting the proper models, good location, good styling etc) and of course the photographic execution (lighting, exposure, composition, focus etc). Surely retouching has its role but it cannot make the image. E.g. it cannot turn just any woman into a fashion model or make any piece of cloth look like a $15k haute couture dress. Obviously even when the shot is aesthetically and technically excellent, there are still things which need fixing in post but those are quite different from correcting the mistakes of the MUA or dirty studio background repeated on 20 images etc. When you shoot with the retouching in mind, you can reduce the time ($) needed for it which makes your whole process more efficient and the result will obviously be better.

There is a common misunderstanding that the retoucher must have a certain style and that based on that the client picks the right retoucher. That is very wrong. The retoucher is NOT an art director, he must NOT influence the image with his personal subjective preferences. He must be able to see and understand the overall style of the client (or the style the client is aiming for). In any case an artist needs to be free, not dependent. So don't let the retoucher or anyone else, however reputed, give the direction of your work. It is your work.

@OP feel free to email me if you have any specific questions regarding any particular images of yours and I will do my best to share with you what I see. Note: this is not an enticement. I don't charge for answering email

Square Jaw Photography wrote:
That's essentially what just happened. I provided clear instructions on what I wanted done, but in the end, I was disappointed. I want to know my photos will come out good when I invest that kind of money.

Maybe you have picked a wrong retoucher... or you have too much expectations when it comes to retouching. Remember that retouching in not there to fix photographers mistakes, but rather enhance a good photograph and make it into a better one.

Square Jaw Photography wrote:

That's essentially what just happened. I provided clear instructions on what I wanted done, but in the end, I was disappointed. I want to know my photos will come out good when I invest that kind of money.

I don't know how much you have invested or what your requirements were, but as anchev said, the whole point is to free your time to focus on other aspects of your job. It's not about "can this person amaze me every time", it is about "can this person deliver what I need so that I can delegate and have free time to expand my business further".