Insurance Hell

Since I'm turning 26 this year, I am getting kicked off my parents' insurance in a few short months. (Which is kind of a blessing, because I'm the only one on our family plan that ever goes to the doctor and therefore I get stuck paying the deductible for the whole family every year.)

But it's mainly a bummer, because that means figuring out how to get myself some coverage, since being self-employed doesn't lend itself to getting free insurance.

I've done some research about potential plans, and I will probably stick with my current provider, and just get my own plan. Should make things easy? You would think, but I foresee two potential problems:

1) In order for said company to cover pre-existing conditions, you must prove that you were previously insured for the 18 months prior to your new plan starting. Which I will have been, but this company does not actually send out the letter saying that you were previously insured until after your policy ends. So what happens if I need to visit a doctor or, God forbid, the hospital before they mail me this letter and I send it back to them? (Because yes, that's what the lady on the phone said would happen. Isn't there a way for them to just pass the paperwork on down the hallway and save themselves — and more importantly, me — some stamps and time and headaches?)

2) I never actually changed my name on my parents' insurance when I got married, because all my doctors had my maiden name on file, and therefore my prescriptions were under my maiden name. When I switched to a new doc a few months after getting married, I tried to put my married name down on the forms, but they said the name had to match the name on the insurance. So I don't know if I should apply for the new insurance under my married or maiden name, or if I should try to change my name on the insurance now before it switches over. If I don't change my name now and put my married name on the new form, will they know I'm the same person and that I was previously insured (see #1)? If I change my current insurance to my married name, will I be able to still get access to my prescriptions, or will it cause a major disaster with the doctors' offices and pharmacy?

I told this story to both of my parents; my mom suggested I change my name with the insurance/doctors/pharmacies immediately, and my dad said he didn't think it was such a big deal so I shouldn't bother to hurry and change my name if it would mess with all my records. So I don't know whose advice I should take!

Anyone work in insurance and know how these things work? Or have you dealt with finding your own insurance plan? I am terrified that there will be some kind of problem.