Buy in now so you can receive the June dividend.
Buying so that you get the dividend doesn't makes sense. The share price just goes down by the amount of the dividend. And then you pay tax on the dividend.
Buying because it's most likely to go up over the short and long term is a good idea. Just not dividend timing :)
+1,000
Given the option, I would much rather purchase just after a dividend payment, not just before. If I was trying to maximize my tax burden, I might think otherwise.
I think you have to look at where you are in comparison to the record date. Using March VTSAX dividend, even with accounting for tax, you would be better off purchasing from on any day from March 1 - March 10 than if you purchased on either March 14th, 15th, or 16th. (March's dividend had a record date of March 11, Reinvestment date of March 14, and payable date of March 16.) And you will continue to be better off if the dividend is reinvested due to the compounding of the additional shares.
True story. I don't recommend dividend timing, and the tax effect of a quarterly dividend is not neglibible, but pretty small. I'm just not a dividend fan, and investing simply to get or avoid a dividend is silly. When I say I'd rather buy right after a dividend is doled out, that doesn't mean I would wait. I'd just prefer that it worked out that way.
I've written about the effect of
tax drag, and if you invest in a tax efficient manner, it's pretty small. For me, currently in a high tax bracket, it's about 0.6% per year, or 0.15% per quarter. Since the market usually moves more than 0.15% per day, timing around a quarterly dividend isn't particularly useful. I'd rather not pay the tax, but I'm not going to wait to invest to do so.
Best,
PoF