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There are many retirement calculators on the net but they all seem to be at a very high level asking the same standard few questions. I am in my early 50's and looking at retiring at 55. I met with a finance guy who typed in all my investments etc and showed me the results the program spat out. This is okay but I don't have access to his 'fancy' program and would like to in my own time manipulate values and scenarios.
I am looking for a DETAILED retirement program/system/tool where I can enter all my values for local shares, offshore funds, RA's, assets, monthly contributions,  when I want stop contributing, inflation, expected funds growth, expenses, planned holidays, buying a car in retirement ...etc etc etc.
Anything like that out there?

One of the members has a very detailed one somewhere on the site. It had field for Ra, tfsa and regular investments. Will find it for you later.

This one is very frustrating. Firstly, do you remember that policy you took out 20 years ago where the "sales" guy told you that one day you will get R50 000 and you felt you will be rich and now today when it pays out, you can do absolute nothing with it and laugh your head off for being suckered into such a stupid thing? Well retirement calculators are the same. And don't get me started on inflation. Inflation is the biggest rubbish under the sun. You would do far better looking at the CPI (Consumer Price Index).

Well back to the original topic. If you have an investment and it gives you X amount every month, but the day-to-day living costs keep increasing by Y every month, you will reach a point where your pension just won't be enough. Let's take a very good example. My consultant told me that just doing a quick calculation, a million bucks should give you an income of +-R6000 per month(non-aggressive investment). Well just looking at medical aids that increase by 15% or more per year, will your investment ever be enough. If your investment does not give you income = to CPI increase on a monthly basis, then surely you will be worse off next month and the month after that and the year after that and so on.

 What I am trying to say, the cost of living increases on a month to month basis far faster than inflation and all these calculators use the inflation numbers that are wrong!

and just to make me angry as a bat:

If an average investment as I stated above can give you +-R6000 per month per million invested:

R1 000 000 = R6000 per month
R100 000=R600 per month
R10 000=R60 per month
R1000=R6 per month ? Really. You want to tell me that these financial guru's can't get us more than R6 per R1000 invested per month?

Time2Retire - the most important pointer I could give you is to take stock of your financial standing right at this point in your career - thus list salary, benefits, special awards, and bonuses (shares or cash), R.A's, Mutual funds, Life Policies, endowments (if you have any), leave accumulated, retrenchment package that the company may offer if retiring at 55, any penalties if you exit your pension fund early etc.
List all these income streams, plus any longer term liabilities that may be in play beyond your retirement horizon age.

I would create a spreadsheet of all your income streams salary and allowances for cast at 3% growth to age of retirement. Then determine from your HR department what portions of your salary package fall away upon retirement and what is your likely pension payout as a percentage of your gross income. If you get anything above 70% as a percentage and that they will give you an annual increase at the CPI rate whilst in retirement, then you will live comfortably. If you have wealth beyond this and you invest judiciously you will survive quite handsomely in your later years which is why you need capital and investments beyond a stable pension program.
I can't see a financial calculator working out whether you can or can't retire at a given age that is totally dependent on present salary what you lose from that gross salary and what your liabilities are currently and how quickly you can liquidate such liabilities. Also as a warning never cash in a portion of your pension to liquidate your liabilities as you will never regain that capital and all future CPI awards will be based on a lower pensionable income. If you have a bond extend its repayment end date - mine is to age 75 and I use it to purchase shares, or to do large property maintenance and repairs, and/or  my latest to settle the balloon payment on my car loan.
My advice be creative in using you finances - I turn 70 this year so nobody is going to employ me so I can't generate a new income stream unless I turn my hobby into a business which I have no intention of doing - I retired at 58 and am thoroughly enjoying myself
So best advise do you own sums and underestimate your returns on the income side and overstate the interest rates on the liabilities side of your calculations - some like to call it worst case scenario