Dexie, don't get a tattoo from somebody who may have only been doing the work for 2-4 months. Get it from somebody who has done it for at least 2 years, those who actually go through apprenticeship and able to do clean lines and give you the desired work that you are wanting.
I have 2 tattoos myself and I do not regret getting them, in fact I plan on getting more but who I get mine from have been in the business for more than 6 years and are well experienced. I understand you know the guy and you may want to help him out but I wouldn't get something from him.
If you do decide to get something from him, have it be small such as writing or a symbol that relates to you or your life that way it's small, he gets his practice, and you get a tattoo that you both are happy with.
Oh shit. I kind of expected this but not for awhile. You've been a great staff member here and a loyal friend to the community for several years. You've been here just as long as I have and I will truly say, you've been a great friend. Good luck brother.