These are all great points you are making.
Here is my reflection on it.
Anyone can be an entrepreneur but a lot of times what I see is that entrepreneurs are created out of situations. Cause and effect type situations.
for ex: You grow up poor and swear you will ever be poor again so you start your own business.
You hate authority figures and people telling you what to do, so you start your own business.
You seek life long adventure, so you start your own business.
Being that you are the second generation within a family business, you might have not had to deal with such issues because you might have a strong willed father possibly that pulled this business all together and made it happen.
This may not necessarily apply to you, but this happens. You grow up in a business and you don't develop the skill or confidence to go off on your own, because you didn't have too.
Because the skill set hasn't been developed yet, a low self esteem may exist that makes you question whether anything you do is valuable to anyone.
When you reflect on this statement:
I guess it factors in Will my service be worth the price to the customer, Will I be able to build a good trust worthy bond between the owner and myself. Heres another good one, Will he rep me to his buddies or talk about what he dont like?
Do you find this to be the case? Or do you feel it is because of another reason?
Knowing there is an issue, figuring out what it is and why it is can help you move forwards and overcome it.
I know that many forum readers are in situations where they question their value and what they can offer and it keeps them from doing what they really want.
The beautiful thing about all of this to remember is, it can all be overcome. I know you are going to do a great job and you will kick ***. It's just getting over this mental hump and moving forwards.