I will have to pay a lot in taxes this year. Still need to do them... For health insurance I have a high deductible plan that comes out to about $280 a month for my wife, son, and I. We also keep about $5k (and growing) in a medical savings account to meet the deductible.

It probably makes sense at this point to talk to an accountant (if you don't already have one). I don't know how your business structure is set up, but you may want to look into setting up an S-corp and/or a retirement plan like a solo-401k.

$280 a month? Is that maybe an employer plan that your wife is on? If not, I've got to get more agressive in my insurance shopping. We haven't gotten a quote below $1000 a month for a family of four.

That is an individual plan for myself, my wife, and our 1 year old son. We are both young (22) and have no health issues. Also it has a $5k deductible and we live in an inexpensive state (Idaho).