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 choosing shares, after which afterward purchased some extra primarily based alone analysis.

Nevertheless, I’ve lastly realized that I used to be doing all of it flawed to start with – I’d have been a lot better off in the present day had I invested recurrently in some low cost low price ETFs as a substitute of betting on particular person shares. Whereas a few of my shares corresponding to AAPL,MSFT,GOOG and many others. appreciated considerably, a number of haven’t completed so properly corresponding to DIS, BA, DAL and many others. Total, my portfolio has appreciated however it’s positively wanting 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 hold hold it easy by utilizing automated investing. Nevertheless my principal dilemma right here is learn how to take care of the tax implications for such a significant transfer.

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

I lately bought off many 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 web realized long run features 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 number of index primarily based ETFs. My goal could be to maintain my web capitals achieve round $10k or much less in a given tax yr. (I’m within the 15% tax bracket for capital features, like most different folks)

So the large 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 up to now with the belief they might not be capable of maintain the momentum sooner or later – ideas ? I suppose an alternative choice could be to promote a sure proportion of all shares till I hit my capital features 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 suggest.

Thanks upfront !