When to pay capital gains for greater diversification

[bamsphd]

I will soon receive in kind with no step up in cost basis
the shares of 37 different companies.* These shares have
mostly been held for decades, and almost all of the tax
losses have been harvested.* My tax basis will mostly
be between* 50% and 1% of the current market value.

While the companies have not been bad investments,
(the portfolio manager harvested all the mistakes) I would
prefer wider diversification, both in the sense of more
stocks through Vanguard index funds, and in the sense
of more asset classes.

What I don't know is what algorithms to use when deciding
how to value the cost of incurring capital gains taxes now,
versus the benefit of better diversification.* Can anyone point
me to any articles or discussions on this topic?

thanks,
Bill