re: Am I over thinking this...Roth v. Traditional IRA

Set up a business for your timber income. Then you can set up a solo 401k or SEP IRA and contribute up to 54k a year tax deductible.

If youre in the 33% tax bracket, dont you make too much to contribute to a roth?

As someone said, read into roth conversions. You can choose to pay taxes on IRA money and transfer it to a roth. Its very popular for my 60 to 70 old clients now that taxes are low. Also decreases your RMDs at 70 1/2