My birthday is next week. I've had the stark realization I'm not quite where I should be with my retirement, and whoa buddy. Thats a hot poker in the ass to get motivated!

Current situation:
 Fidelity:
  Company provided 401k
  Rollover IRA

 TD Ameritrade:
  SimpleIRA

 Vanguard:
  Roth IRA

My 2 big questions here are whether I should consolidate everything with Fidelity and how can I make a post tax contribution to a pretax investment vehicle...ie...How can I put money into my rollover IRA or SimpleIRA? 

A big more on that, I have no compelling reason to roll everything into Fidelity outside of ease of management. Having 1 web portal to log into to manage all my investments would be a bit more convenient than having 3 different web portals to log in to. The contribution bit really confuses me. IRAs are supposed to use pretax dollars (I thought?!) but I have no way to set up a pretax deduction from my paycheck to make contributions to anything outside of the company provided 401k. If I do make a post tax contribution (Write a check) do I end up claiming that on my taxes or some such and get a reduction on my income for purposes of filing taxes?

I had briefly thought it was nice to have more than 1 company to have investments in, sort of an "Eggs in one basket". If 1 company were to utterly fail it would protect me a bit. Then I realized if it got to the point the assets of one of these major players were completely wiped out....Well, everything else is probably not far behind because thats something of a "game over" event I think!


Anyways curious how to best get this all cleaned up....Or whether I should do nothing at all?

you need to talk to a cpa about the specifics but you can contribute, depending on your age, quite a bit to the company 401k.  Talk to your HR about contributing more.  The simple IRA and the role over could be combined I believe if there is any advantage.  After that if your income is not too high you may be able to contribute to a ROTH with after tax dollars.  First max your pre tax contributions.  I am not a professional tax or financial adviser but that is my dog sense on the matter.  I do what my CPA says I can do.  lol

The only reasons I see to do anything is if you strongly prefer to have one web site to view all of your investments, or one company offers investment fund options that you want and one of the other companies doesn't have that. Another reason could be fees and expense ratios, but I don't think any of those three are terribly expensive, although Vanguard is probably the lowest.

do you use any of the three firms research? Or do you wing it?

I do a bit of research but honestly I am aware enough to realize I cant beat the market. I follow a general "3 fund" strategy although I dont adhere to it strictly....ie...In the TD account I have I 5 funds rather than 3. 

Other than as you state, convenience, the first reason to consider consolidating everything at Vanguard (eventually) are lower expenses (I haven't checked Fidelity's expenses in a long while, but Vanguard has the lowest expenses in the industry; Fidelity may match them here and there, but fund for fund, Vanguard will charge you lower management fees).  The second reason to eventually consolidate everything in one place is RMDs:  once you reach 70.5 you will be required to start emptying your (non-Roth) IRAs; while wherever you have your $ scattered should compute your RMDs for each account, it's much simpler if everything ends up being rolled into one account.  The only reason not to merge a rolled over 401(k) with your IRA(s) is if you think you might someday want to re-roll your 401(k) back to an employer plan...which IMO is a) not likely ever especially since it's already at a good place like Fidelity and b) isn't possible (without some complications) once you retire and/or reach 70.5.

To make non-deductible contributions to your IRA(s) you simply transfer the $ in (send a check, bank transfer, however) and complete IRS Form 8606.  It doesn't count for anything except someday when you withdraw it you won't be taxed on it but guess what?  Since the IRS wants the tax $ you avoided paying all those years the taxable $ has to be withdrawn first.  Thanks IRS!

How much you can contribute to IRA(s) depends on your age:  if you're less than 50, you can contribute a maximum of $5,500.  If you're 50 or more you technically are not eligible to contribute to an IRA but you can make "catch-up" contributions of up to $6,500...so $5,500 up to 50, $6,500 50 or over.

You can put just over $17,000 into your 401(k) every year, unless your employer has some crazy rules and you're one of the higher earners... You should also be able to add $5,500-6,500 to your IRA depending on income level, you'll need to talk to your CPA about that

Typically, you get a lot from diversifying your investments, but all you get from diversifying firms is paying higher commissions and annual fees. You don't have to keep all your eggs in one basket, but you want all your chickens on the same farm, so to speak. Pick the one you like the most and go with them. There's research to show that around 95% of successful investing comes from asset allocation and time in the market, actual investment selection is around 1% of your overall success.