skipro33
Thinks s/he gets paid by the post
Tax payments: Not quite. Unless you have a way to get the taxes paid via IRS withholding, you need to make even quarterly estimated payments, or pay as you go. The even quarterly payments can be based on this year's estimated taxes, or last year's actual payments. Look up "safe harbor" rules.
I'm not big on market timing, but if you can catch a downturn and do it then, that would be a good play. Really, whatever way you want to do it is fine. It sounds like you're only dealing with a small part of your investments.
Yes, I do have a way to pay the taxes via an IRS withholding. I could make monthly IRS Tax payments via my pension or I could make a fixed payment via my SS.
I have H&R Block tax program and can play 'what-if' with that on funding a ROTH and timing the tax payments. I have already started my taxes and I owe a small penalty, $3, because I underpaid by $1,000. But the program asked me if there were circumstances that might be weighed, such as; did you fund a ROTH? So I will test this with this year's tax program to learn about when to time the funding and the tax payments for my best options.
Thanks again for pointing all this out.
Last edited: