Freelancer Tax & Financial Questions

Hey gentlemen,

This is my first post on this board, but I have been a lurker for a few months just trying to get up to speed on the various terminology and what not.

First off, let me just say that I know that I will ultimately need to talk to a financial planner or a CPA to get me really going, but I figured I could get some advice here at the very beginning to sort of provide a direction for myself.

I currently hold a full time job that I plan on quitting in September for a full time freelance gig.

I have a pension and 401k at my current gig, as well as great health benefits. I understand that this will be a sacrifice, but I'm willing to do it for peace of mind.

Our department is being eliminated eventually within the next year, so I figured I'd rather exit on my own two feet in good standing.

Okay, so that's the backstory.

My new freelance gig is as a blogger, so I will be working from my home office, from Starbucks, etc.

Who should I talk to about taxes? CPA, Financial Advisor, etc?

I know I will be to write of a portion of my home for working (Home office).

What about healthcare, I will have to pay out of pocket, likely 3-400 monthly. How much of that can be written off?

What about my investments pension and 401k, should I roll into a Roth IRA, or a regular.

I think I will make about $3000 a month flat, with no taxes taken out by freelancing. I guess I want to get a grip on whether or not this is feasible, and how much taxes will bite me.

Is there any legal way to take enough deductions that my taxes don't sting to the point where I can't make a living?

Sorry for som many questions, I'm just trying to get a good idea on where to start.

S.