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I recently went for a medical assessment, and my prior doctor guessed I had some form of personality disorder. This time, with more information (which my sister gave), the new doctor wondered if I may have Asperger's.

I done a Asperger's test online ( http://archive.wired.com/wired/archive/9.12/aqtest.html that one) and I scored 42 out of 50, with 32 + saying you're very likely to have Asperger's. But when I did some more reading on Asperger's, I don't think I match all the criteria.

They say people with Asperger's may say things that upset people, like say their hair-do makes them look ugly, or something like that. They don't do it with malicious intent, they just don't understand that it upsets the person they're saying it to. I don't recall being like that.

On the other hand, I have always been painfully shy, I really dislike making eye contact (if I do, I look away right away). Even with people I've known for years, including close family members. I have little focus, like ADHD, unless it's something I'm really interested in, then I can spend a lot of time researching it, kinda like the hyper focus that's talked about. I notice tiny details in things that other people don't, and if I talk about something, I do the reported 'one way' talk where I go on about something until the person tells me to shut up, like about something I've been researching. I had trouble learning simple things like tying shoe laces, reading a clock until much later than the other kids in school. I couldn't understand grammar (commas etc) through high school, even though I was in a lot of the top classes, and I only learned how to use commas etc properly, when I taught myself online when I was like 20.

Do I have several medical issues (personality disorder + ADHD, OCD) that just so happen to outwardly seem Asperger's-esque?

And to put this in perspective, I've not had a real, physical friend in around 10 years.

Could you ask your doctor for a referral to a specialist if you want to find out for sure?
With regards to saying things that upset other people - that's an extreme example and not necessarily part of the criteria for ASD. Females especially would quickly learn that that kind of comment is unacceptable and adjust accordingly.
The rest of what you wrote could have been describing myself.

Being unintentionally rude is one way of not knowing how to communicate presents itself. Not knowing what to say and thus being afraid to say anything and being painfully shy is another way not knowing how to communicate presents itself. The core Aspergers criteria is not knowing how or atypical communication with others. You have several other significant traits associated with Aspergers. Even if you have Aspergers it would not rule out having other conditions. I would advise continuing to pursue figuring out if you have Aspergers.