All in all it is far better to do your own withholding and set aside X% of every check into a “Tax” account, then draw from that for your quarterly payments.

@sarah – Amen, sister. When you owe a lot of taxes it’s usually because you’ve been blessed with “lots” of money! And it’s not like we didn’t see it coming, even if we did our best to ignore it ;) I can think of a ton more horrible things that come when you least expect it. We just gotta suck it up and continue to work our a$$es off. Hope you get your issue corrected!
@David – Haha, YES! That’s brilliant man, so glad you found SEPs too :) You’re right, not the most glamourous part of the job, but it is what it is and we keep working on fine-tuning that right plan to keep the headaches away. Thanks for sharing bro.
@Elle – Thank you Elle :) You’re too sweet. I hope you have a rock star 2011 too!!
@Diane – I now believe it ;)
@HedgeHoncho – haha, exactly.
@Wade – That’s right — gotta get the plan on track for the big day! :)
@Mike Piper – Very true. I’ve heard the benefits of S-corping.. can’t remember why I decided against it for now, but I’m not taking it off the table for later. We’ll play it year by year :) And good call on the quarterly specifics, yes – forgot already about that, haha…
@kay – Thanks Kay! I really appreciate you being here :)
@Diane – Hello again :) That’s a very good question actually, and I think you’re right. My accountant initially told me I was probably gonna get fined for holding back on all that cash last year, but then she didn’t mention it specifically when we were going over the results… I’ll check the final paperwork once I get it, def. something to consider.
@Alotta Lettuce – Ooooooh not bad, not bad. I’ll talk it over w/ the wifey and see how are deductibles are looking… haven’t had much time to go over our new insurance (it’s through her university).
@Evan – Well, we’re getting there ;) Set up the LLC early last year, but still ironing out the ways to be most efficient.
@Brian @ Be Better Now – That would be nice! And you’re right – I’ll keep padding it and just take it as a nice surprise if it pans out :)
@Mercedes – Yeah, do it! The only way I found out was through my accountant, so if he does his own taxes he may not know about it. I’m incredibly excited, as you can imagine ;)
@Lauryn – Welcome to the club! I hope you get even better knews than I did :) It’s very scary indeed, but you’re not alone.
@Tim Anderson – Freaky, huh?! But the good thing is that we only have to feel that way once :) Now that it’s all over we can plan and prepare for all future years (and quarters). DEF check out the SEP stuff, and make sure if you go for it that you do it before April 15th and put it toward 2010. Unless you want a leg up on 2011!
@Jon the Saver – haha, nah man I can’t hate on ya. I’ve been getting G’s back for years ;) And did pretty much the same thing as you — save/invest that money away! It may be boring to some, but it’s not their lives – it’s yours. You gotta do what you gotta do, bro!
@Andi B. – Nicely done! Hopefully I can get my stuff down like you have, that’s impressive :) And oh yeah – it’ll still be dented, just in a much more peacefully way, haha…

Ended up getting a tax return of 7k. I was pretty boring with it through, went straight to the Roth and paying half my car loan off.

Man, your taxes are complicated bro!