First of all, if your plan offers a designated Roth option, you are better off contributing directly to that option than making after tax contributions into the pre tax account.
Also, you need to determine both the circumstances and the class of funds that you are allowed to distribute while still in service with this employer.

For example, IF they allow only after tax contributions with their earnings to be distributed or converted, then some earnings will be part of each conversion and the earnings would be taxable. The taxable percentage should be based strictly on the class of funds allowed to be distributed, so if the pre tax contributions and their earnings CANNOT be distributed, then they should not affect the taxable amount of the funds that can be distributed or converted.

There is no 8606 or similar form that applies to direct conversions from an employer plan. You and the IRS will be guided only by the 1099R issued by the plan administrator. Since there is considerable variation in how the plan is designed, it is advisable to direct this question to the plan administrator or reseach the summary plan description to determine what that 1099R will look like before acting. Otherwise, you will receive the 1099R in late January where it is too late to change your mind.

Your age should not affect your options, although broader options might apply to those at 59.5 or perhaps some other age in their 50s or higher.

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