"my understanding is my by-back was treated as a Roth" - that might be true if it were a separate Roth account, but in this case, I think it is just after-tax contributions in your pension (this is called "basis)". But there is a lot of similarity between a Roth and the basis in your pension (but don't read too much into that).
"Early & later contributions- annuity/pension money was deducted pre-tax from payroll, when I started at 19, I earned $800/month, hence the $50/month, as years passed the amount increased, as I neared 30 + years the amount was over $300/month deducted pre-tax" - OK, since this was all pre-tax, we won't care about that. What we care about is determining the amount of after-tax money in the pension (i.e., the basis).
"I did answer regular distributions for the pension plan, it’s the same plan I’ve been drawing on for the past 10 years " - OK, if you had applied the Simplified Method to each year, you would have been calculating the basis returned to you each year. This is one of the questions in the interview for the Simplified Method.
However, I am thinking that you have not done this before, so when you are asked how much basis had been returned to you, you will have to answer zero.
In any case, enter the 1099-R for the pre-59 1/2 first, then the other 1099-R. If there are any questions in the interview about your pension. call the pension administrator and see if they will tell you.
In the worst case, you can just declare the box 1 amount as the taxable amount (see waaaaay above) - you would enter up paying tax over the next 10 or more years as the $60 +$160 are treated as taxable income spread out over the remainder of your natural pension, so a small penalty to pay if it allows you to file.
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