Tax question (capital gains, student loans, etc.)

Alright, obviously I’m going to have to speak with a tax professional (and, um, file late), but if somebody here could give me a vague idea of where I stand and what I can expect, it would be much appreciated.
Late last year we finally cashed out my college fund. I graduated five years ago, but I’ve been deferring the student loan payments until recently (total debt approximately $25K before any payments). 12-15 years ago my mother invested roughly $10K in the stock market, and we cashed out roughly $42K. The investments were in her name, but when she cashed out she had the brokerage firm cut a check in my name, and the money hit my checking account. After the new year I gave $11K to my stepfather to help with his (frankly horrifying) tax problem, used $8.5K (also after the new year) to pay for a year’s rent, and have been making incremental student loan payments with the remainder (about $1K a month).
Again, I’ll certainly have to speak with an accountant, but if anyone could give me some idea about the answers to the following questions that’d be great:

– What kind of capital gains liability are we looking at?
– Whose liability is it, legally?
– How will my student loan debt factor in, generally?
– What are the implications of my $11K gift to my stepfather?
– Any obvious considerations I seem to be forgetting?
– Any general advice, aside from the obvious (“Get thee to a CPA”)?
Thanks in advance for any help you can give.

Step 1 - File an extension

Step 2 - Make sure you have or get the necessary year end tax documents to show how much student loan interest you paid and the details of that fund you cashed out

Comments…
The gift shouldn’t have any implications.

The way that fund was set up is going to be the wild card.

I missed a key detail in my first read thru … if the fund was in your mom’s name, she’ll owe the taxes. Has she been paying taxes on the dividends all these years?

Presumably not. That actually has to do with the tax problem I alluded to in the OP: Mom and Stepdad didn’t file a tax return for 5 or 6 years, and since the IRS finally realized this fact they’ve been trying to sort out the mess for the past 2 or 3 years.

In addition to taxes on the dividends, your mom will also have to pay the capital gains. Since the gift to you was also more than $10,000, she may have to pay gift taxes as well, but obviously you’ll all need to consult a tax lawyer.