Rebalance shares to index funds - tax implications justifiable ?

I’m a beginner right here, simply learnt about index funds this yr. (please do not choose me)
I began investing in a taxable brokerage account again in 2010 and slowly through the years constructed up a large portfolio of principally particular person shares.
Initially I had adopted a number of the recommendation of Motley idiot inventory advisor for a few yr in selecting shares, after which in a while purchased some extra based mostly by myself analysis.

Nonetheless, I’ve lastly realized that I used to be doing all of it improper to start with – I’d have been significantly better off at this time had I invested frequently in some low cost low price ETFs as a substitute of betting on particular person shares. Whereas a few of my shares akin to AAPL,MSFT,GOOG and so on. appreciated considerably, a couple of haven’t finished so properly akin to DIS, BA, DAL and so on. General, my portfolio has appreciated however it’s positively in need of the S&P 500 efficiency.

I suppose it’s “higher late than by no means” to implement a course correction to maneuver to index funds and maintain maintain it easy by utilizing automated investing. Nonetheless my most important dilemma right here is learn how to cope with the tax implications for such a significant transfer.

My present portfolio worth of taxable account is about $680k with unrealized positive factors of $380k. ($189k of those positive factors are from simply 4 shares that I intend to carry onto for now – AAPL,MSFT,GOOG,META)

I lately offered off a lot of the loss making / in addition to a number of the underperforming property for the aim of tax loss harvesting, however even after the offset I’ve internet realized long run positive factors of about $9k already. I’m considering of following this technique yr over yr subsequent 5-7 years till most of my particular person inventory positions have been rebalanced into a couple of index based mostly ETFs. My goal could be to maintain my internet capitals acquire round $10k or much less in a given tax yr. (I’m within the 15% tax bracket for capital positive factors, like most different folks)

So the massive query could be which shares ought to I promote first – those which have been constantly underperforming the market or ones which have carried out properly to date with the idea they could not have the ability to maintain the momentum sooner or later – ideas ? I suppose another choice could be to promote a sure proportion of all shares till I hit my capital positive factors restrict for the yr.

Has anybody confronted an analogous state of affairs / dilemma ? How did you go about coping with the state of affairs ? What method would you advocate.

Thanks upfront !