I beg to differ, I had the same attitude for many years. Doing taxes pointing out how much better it is to owe than receive. I reached a saturation point where I was paying a penalty & fees for that view. After retirement, my income versus expenses were drastically reversed. I had a 401K, retirement pension (annuity) & SS. Our downsizing & move resulted in more savings. Because of 'my previous poor financial planning' I found myself mired in debt, coupled that with the big loss in our home sale. I was able to recover taking out most of my 401K, paying down or off most of the debt. Some went into savings but here was the kicker, the savings account was paying an embarrassing rate of interest. Less than a penny on the dollar.
If you owe both state & federal more than the allowed limit you will pay fees & interest negating any return you could have received from the savings. I found that my needs in retirement were less than expected, income was more so I adjusted my pension & SS to increase withholding. We are still able to save $500 monthly in our long term savings, put some away for emergencies & deposit more than $3,500 annually from the returns. We have built up a nice nest egg for my demise paid off all debt, mortgage free (we do pay space rent), we are not beholding to anyone, haven't had a car payment in 3 years. I don't worry about the whims of the stock market, real estate market & only address or attack any bleeding from my budget through adjustments to utilities/living expenses.
We could still travel if desired but our choice of residence is located in the same general area we used to vacation at. Great weather, low crime, friendly neighbors, less congestion, clear skies, excellent health facilities, no state tax on SS, no sales tax, low property taxes (<$6.00 annually), no bogus auto inspections & lower licensing fees than most other states. It takes a visit to the local SS office with form in hand & less than 3 minutes on line to change my pension exemptions up or down, so that is a non issue. I just went from 10% (SS) to 15% for 2016. My returns are simple & free with only income to report, no deductions, no credit cards, no rewards to declare. By avoiding other 'shell' games & scams I feel my retirement is becoming stress free.
Something that makes more sense to me would be to invest $20,000 into a high yield stock that's paying a 4% annual dividend. In Jan of each year withdraw or cash the dividend checks for the $800 earnings file an estimated tax form by the Jan due date. Wait until April 15th to file your taxes (that way you would have 4 quarters of dividends) thereby owing nothing with no penalty or fees. Any favorable return from the sale of the stock you hold long enough to be considered a long term invest would put more money in your pocket.