either a 401(k) or a 403(b) or something similar, right?
You may be way ahead of me here, but I just want to make sure I'm clear, as what you wrote above is just a tad confusing.
If you'll indulge me, allow me to pick your post apart!
One Reason We Didn't Go with a Roth was because the money has NOT been taxed and when we withdraw we know we will have to pay the taxes. But paying taxes on a smaller amount later than the total amount yearly will be less.
Weeellllll....maybe! It really depends on what happens to tax brackets in the future as well as how much on an annual basis you project you would be distributing from the traditional IRA when you retire. Now I want you to know, I am NOT giving you advice here one way or another, just trying to make sure you are clear on your options. If you did do the conversion you are right in that the taxes due would be a big hit now, but the thing is, it may be less that the total paid over time later on. Like we both know, when you take a distribution from the Roth you will owe no tax at all, which has a kinda nice sound to it! Plus, with a traditional IRA, you have the "RMD" to worry about (Required Minimum Distribution) every year. You HAVE to take some out after 70 1/2 years old whether you need it or not. There is NO such requirement with a Roth, plus a Roth has other advantages with regard to beneficiaries, for instance. It is something to bear in mind.
This much I know because the money has been saved from a pension plan then rolled over to MSSB. A friend of ours said it would be more beneficial (as a profit) as opposed to simply setting up a traditional IRA.
This part is a bit confusing. When you do a rollover from a defined contribution plan (another name for 401(k)'s and 403(b)'s), the IRA that receives the funds is often referred to as a "Rollover IRA", but for all intents and purposes, a rollover IRA is exactly the same as a traditional IRA, at least from a tax and distribution perspective. If you had rolled from the previous plan into a Roth at that point then yes, you would have had the tax liability. Rolling to a traditional (or rollover, whatever they want to call it) IRA is the most common procedure and there is nothing wrong with it at all.
So, I sit and watch the market from time to time, but NEVER "play" with placing bets. Some have told me it's easy, but I'd rather not. I do have a couple of friends who play all the time, but lately some aren't so happy.
Completely understandable. Picking individual stocks is not easy to get right. That is why Mutual Funds are so effective for the average investor and their
long term investing. They are managed by (usually) a team of people who do nothing but research stocks all day. You basically have professional money management on your side and you pay a comparatively small fee for it. Having said that, one mistake most often made by the average investor is to panic during times like this, sell out of the Mutual Funds they own during a downturn and then buy back in when the market recovers and they feel comfortable again. The old "Buy low, sell high" idea thrown right out the window! If you own one of the common, Large Cap "Growth" type mutual funds and you are reinvesting dividends and interest(if any) then that happens all the time, so even when the share price is down, you are buying more shares at a lower price automatically. With mutual funds, a long term time horizon is best, and by that I mean AT LEAST 5 YEARS, better off more like 20.
In case you aren't aware, here's a website which can give you all sorts of information about the funds you own, all you need to know is either the full name of the fund or its 5 letter symbol. All open end mutual funds have a 5 letter symbol ending in "X". All of them.
www.morningstar.com
I wish you all the best.