Edit: Those 5 and 11 month dates would also be the dates the holding periods would be met.
Once that happens, the whole gain from $88 to the selling price would be taxed at a LT capital gain AFAIK
For context, I'm in early career, and those shares are ~40% of my investment accounts and ~30% of my total net worth. I have a fully funded EF and maxing out all available retirement accounts.
This bolded bit is probably not true. The taxation of these ESPP plans is a bit complex. See
my post from an old thread about how it works.
No matter how long you hold the stock, ESPP shares bought at a discount will have some income taxed at regular income rates when you sell. Before the holding period is met, the entire discount off the
purchase date fair market value is taxed as regular income. After the holding period is met, the entire discount off the
lookback date fair market value is taxed as regular income. The applicable fair market value will also generally be your cost basis, and you'll pay capital gains tax on the difference between your sale price and your cost basis.
In most cases I'd say that you should just sell the shares immediately because most of the benefit of the ESPP occurs on the date you buy the stock for a discount; any further tax benefit from meeting the holding period is pretty minimal in comparison to the discount, and requires you to hold a potentially volatile investment for some time in order to get it. The risk/reward just isn't there in most cases. However in your case the difference in fair market values on the two applicable dates is quite large. The larger this difference, the more likely that waiting for the holding period to elapse before selling will pay off. It's still a risk, but one that's a bit more worth taking.