Should I stay or should I go???

To sum it up, I have a love/hate relationship with my job. My job really sucks from January to April and then sucks again from about October to November. When the job sucks, it really, really sucks. However, when it's not one of the months specified above, it's a very laid back environment with a ton of flexibility. I've been at my job for over 7 years and I wonder if I have stayed too long. A coworker has already confided in me that it is his last tax season and is giving his notice on April 15th and keeps encouraging me to do the same. He's been talking with a headhunter and the headhunter just laughs at what he was getting paid for his position and really laughs at what I am paid for mine. Apparently I am about $20 - $30k underpaid - wow!!! That's a huge difference and I am completely torn about what to do. A part of me is really excited about leaving this job and jumping into the corporate world, better pay, no more horrendous tax season hours, freedom to take vacation whenever I wanted. There are definite benefits to jumping ship. On the other hand, I have amazing freedom at my current job, due to constant understaffing, they give me alot of leeway. During nontax season, I don't work 8 hour days, get to work around 8:30 (I confess, I get there at the same during tax season but I do stay later to make up for it), take a 2 hour lunch, leave around 4:30 and spend a large part of my day goofing off. I know the issues that surround me at my current job, I know the pros and cons of the job, but if I leave and go somewhere else, what if its worse??? I'm so confused about what to do and I wish I had a sign that would show me the correct path I should take. I'm planning on starting clomid in April/May to get pregnant so is this the best time to be looking for a new job? Is it fair to my new employer to take a new job when I know I will be missing alot of work due to fertility treatments and/or possibly needing maternity leave soon (I'm trying to be optimisic)?? Or then again, is it stupid to stay in a job where I am not 100% happy just because I am undergoing fertility treatments and I know they will give me all the time off I want plus would be super flexible if I ever did actually have a child? I'm just so confused and feel a little silly postponing my future based on what if's. What if I am doomed to constantly miscarry and never have a child, if this is my fate then it seems really stupid to stay at this job. I thought I had my sign in August when I found out I was pregnant again, I thought that was a sign to stay where I was b/c they would be flexible and probably would let me work from home. But now, I'm unsure of what to do and I HATE uncertainty. I'm not going to talk to the headhunter until after April 15th about my possibilities so maybe a sign will magically appear and guide me in the right direction because I sure could use the help right now.

On another note, my mother asked me last night if I had read the article in the paper a few weeks ago that said caffeine causes miscarriages. Ah yes, Mom is still on the hunt to find a concrete reason for my losses, apparently the official diagnosis of bad luck/probably chromosomal abnormalities with the babies aren't sufficient for her. So anyway, she asks if I read it and I informed her with a not so pleasant tone to my voice that yes I read it, I was hoping the tone would get the point across to drop the subject. Nope, didn't work. She asked if I thought my Mt. Dew habit was the cause - ah yes,just another item to add to Mom's crazy list of why I miscarried with the implication that they were my fault. I informed her very icily that no, it wasn't and she finally got the hint and dropped the subject. Not quite a trip to Mom's without a punch in the gut, it'd been over a week since she brought up the subject of my uterus so I guess I should've known it was coming. The good news is that the question didn't want to make me cry so I guess I am healing, instead I wanted to beat her over the head with the article and say why do you ask me such stupid things so I am taking this as a good sign.