401K Conversion to Roth

[Account Closed]

Last year I converted an old 401k of mine into a Self Directed 401k and used that to buy and refurbish a few properties and now the monthly income is very nice and I sleep at night knowing I'm not overly reliant on the stock market.

As I think forward to retirement, I've read several articles about taxation and the goal of keeping taxable income low enough to avoid paying taxes on up to 85% of your Social Security.  With that is the advise to convert existing standard 401k's to ROTH 401k's so you will have the flexibility to determine your taxable income each year and control your taxes.  To do this, however, you have to pay taxes on the conversion at your top rate.  

For example let's assume my top rate is 24% and I wanted to convert 300,000 it would cost me about 72,000 in taxes to convert a 300,000 401k taxable instrument into a 300,000 non-taxable instrument.  

So is it worth it?  Should I take that 72,000 and invest it elsewhere in hopes it would yield more than the tax savings on a 300,000 tax free investment?  Does the anticipation of a looming recession change the logic on a move like this?  

[Carl Fischer]

@Account Closed

Move from forever taxed to never taxed as soon as possible and as fast as possible. I believe it is worth it to convert. I also believe you will pay more than $72k in taxes without some conversion strategies in place. Check with your cpa to be sure. What is your rate of return? Your age? Future income? And do you think taxes are going up or down? What is your break even point? 
investigate strategies to lower your taxes for conversions.