On the one hand, you have the probability of tax rates going up, on the other, the certainty of paying taxes up front. If you have a separate large sum standing by to pay the taxes without cutting into your IRA principal, it might be OK. But if not, your Roth is going to be a lot smaller than your current IRA.
A roth IRA only really makes sense to me if:
1. you are already taking advantage of employer match (free money)
2. you don’t need the money for 5+ years (you can’t get access to liquid cash without being penalized)
3. If you really like leverage (real estate, options etc)
The way we use the funds is to write mortgages to my friends and business partners. He funds my real estate deals, I fund his through the SD roth IRA. We build a 15-20% return into our loans.
You can also use the money for options. buy the optino with $1000 or so, then take the profit from the (stock, real estate) and its leveraged back in for tax free returns.