\was a member on Dave Ramsey's forum but didn't use it enough to warrant the membership fee.
DR charges a membership fee? Wow, if I didn't think he was a scumbag before I sure do now.
Adam, it sounds like you really have your act together and are making solid progress. I don't think you would beat yourself up by having a little fun buying a boat and such.
I am curious about a few things you said though. You suggest that you pay higher taxes on your earnings because they are commissions. I don't see why that would be so. Maybe I am missing something.
I also think that, because of your income, you and your wife probably are not eligible for any kind of IRA, at least a deductible type. And I would avoid nondeductible and roth contributions if you expect you income to remain fairly high because you'll likely end up with orphaned accounts that are more trouble than their worth. You should though be contributing as much as possible to 401(k) plans you might have available.
At this point, what is your total remaining debt load?