Hi Buckeye,
I commend you for taking so much criticism so graciously. You obviously are looking for ways to improve your life's outlook. I see a lot of similarity in my own experience. I did a case study about one year ago and got a lot of good feedback, and also a few harsh (but true) criticisms.
I make a good income, and have a house that is much larger than I need, but I love it too, and this is what I chose to make my priority right now. I also spend a lot on convenience items and gadgets. Some people made the comment that they could retire in 1 or 2 years time if they had my income, and it's true. Other made the comment that I could retire immediately, if I changed my lifestyle. I don't really want to change my lifestyle THAT MUCH.
Many MMM readers have "hair on fire" emergencies where they needed to cut a lot of expenses at once, and they had a great experience doing it. My experience has been different. I get a few good ideas and when I'm ready, I implement. So far, most of my changes have no immediate impact, but as the years go by, I'll absorb more of them, or simply not experience MORE lifestyle inflation.
For instance:
*I'm not going to sell my house because I love living here and it gives me a number of benefits that cannot be counted in $$$.
*I did cancel a few subscriptions that I can live without easily (XM radio, etc.)
*I buy fewer books in favor of using the library.
*I'm not selling my (paid off) semi-luxury car to get a cheaper one, but I will keep this one as long as possible. Based on comments here, I long for the day that I can get rid of it completely and drop insurance payments too.
*I learned enough about credit card rewards programs that I FINALLY traded in my free Amex with 1-5% cashback to Blue Preferred and earned back the annual fee in the first month. I may experiment with some others.
*Learned more about retirement and investment strategies and I'm implementing some of the changes.
My point is that it's about progress, not perfection, so don't let the criticisms make you think this may not be the right place for you. I've almost left the forums a few times, because my spending is quite embarrassing compared to others. But I'm learning and reducing on my timeframe.
When I first joined the forums, my financial predictions told me I had to wait until 74 y.o before I could stop working. I now know a number of ways to change that. Today, without any drastic changes to my lifestyle, I have my retirement planned for age 60 (13 yrs from now). Each day I look at it to see if there's something else I can cut or something else I can optimize to bring that number down lower. And I will.
I think you're doing a great job so far and you have many years in the future where if you just avoid doing stupid things, you'll come out far ahead of most.
Re: the Roth. At your income, why a Roth instead of a traditional? I don't pre-pay any taxes right now because income is at its peak.
Good Luck Buckeye!