Hi @Emitfudd,
Welcome to the Fool.
When I used to work, I always tried to front-load.
When making IRA contributions, I accumulated cash all year then on January 1, I did my maximum contribution. If I could not come up with enough cash, I would try to top-off my contribution as quickly as possible.
On average, the “market” goes up 2 years out of 3. I will guess, my early year contributions and later, Roth conversions followed that ratio, maybe a little better.
Keep in mind that pull-backs are not on a calendar. On average, there is a correction of 10% every 10 months or so. But, we have gone a couple years without one and also had a couple in a rather short period.
Recoveries are also not set in stone.
For the 1999/2000 bubble, our portfolio was fully recovered in April 2002. We owned very little tech approaching the bubble. Coca Cola (KO) was our highest spiking stock.
For the 2007 to 2010 recession, our high was June 30, 2007.(Saturday, logged some dividends and interest) Our fully recovered date was June 25, 2010. Our first stock sale to start to replenish our expense cash cushion was Oct 2010.
For the 2020 correction, Our high was on Feb 22, 2020. Our low was Mar 18, 2020 at -34.82% in less than 4 weeks. On May 12, 2020, we set a new high, 1.21% above the Feb 22 level! We finished 2020 with a 102% gain.
So, I just do it at the first available time. (Ok, I don’t now since I don’t work and all our traditional assets are converted to Roth);
I have seen people get so wrapped-around-the-axle on the “Fear of the Pullback” that they miss great opportunities.
In 2013, a couple people on the old board system were asking if it was safe to invest after the recession. From the time one of them sold out for a 40% loss, they missed a full recoup plus a large gain, like 40% or more IIRC.
They were scared away by all the constant “Doom & Gloom” people on TV commercials and websites.
My 2 cents …
Does that help you?
Gene
All holdings and some statistics on my Fool profile page
https://discussion.fool.com/u/gdett2/activity (Click Expand)