Virginia recently decided to mandate electronic payments. A check cannot be over $1500! Neither my clients nor I have figured out how to use their online site. My suggestion was to mail over-the-limit checks, and thus far they have been cashed 🙂  Another option is to find a 1099 source of income that can "easily" adjust the Virginia withholding.

For federal estimated payments I used to recommend EFTPS online, but that has now become daunting for older folks. It requires some kind of identity verification? One easy solution is to have 7%-22% withholding on 1099-SSA; or collect RMD towards the end of the year and send a chunk to the IRS. Not all 1099-Rs will send any taxes to Virginia, unfortunately.