I just saw this thread, granted it's about a year old, but wanted to contribute. I havent read all the posts, just a few, so apologies if someone else mentioned this.
What caught me by surprise the most, financially, is that you don't just purchase a used car, and start driving it just because you have a license to. I had no idea about vehicle registration or inspections, let alone property tax/title/license plates when you make the purchase. Not only the cost involved in that but the process was a surprise for me. The scariest part is not knowing who to ask to find out about these processes.
I was raised by an alcoholic mother and left home as soon as I graduated high school and literally put myself in a position to sink or swim. I had no idea what was involved in getting an apartment, utilities, etc. I thought you just moved in and paid rent. heh
Another thing that caught me by surprise was filing an income tax return. Had no clue what to do or where to go. It is common sense now, but in the pre-google pre-internet days, and growing up as I did, I had no way of knowing about this. How I found out was I heard people at the factory where I worked talking about their tax refunds and I asked about it.
Going to read the other posts now.. so glad I found this thread!