Rebalance shares to index funds - tax implications justifiable ?

I’m a beginner right here, simply learnt about index funds this 12 months. (please do not choose me)
I began investing in a taxable brokerage account again in 2010 and slowly over time constructed up a large portfolio of largely particular person shares.
Initially I had adopted among the recommendation of Motley idiot inventory advisor for a few 12 months in choosing shares, after which in a while purchased some extra based mostly alone analysis.

Nevertheless, I’ve lastly realized that I used to be doing all of it unsuitable to start with – I might have been a lot better off right now had I invested frequently in some low-cost low value ETFs as an alternative of betting on particular person shares. Whereas a few of my shares comparable to AAPL,MSFT,GOOG and many others. appreciated considerably, a number of haven’t achieved so properly comparable to DIS, BA, DAL and many others. Total, my portfolio has appreciated however it’s undoubtedly wanting the S&P 500 efficiency.

I assume it’s “higher late than by no means” to implement a course correction to maneuver to index funds and hold hold it easy through the use of automated investing. Nevertheless my principal dilemma right here is tips on 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 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 bought off a lot of the loss making / in addition to among 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 12 months over 12 months subsequent 5-7 years till most of my particular person inventory positions have been rebalanced into a number of index based mostly ETFs. My goal could be to maintain my internet capitals achieve round $10k or much less in a given tax 12 months. (I’m within the 15% tax bracket for capital positive factors, like most different individuals)

So the massive query could be which shares ought to I promote first – those which were persistently underperforming the market or ones which have carried out properly thus far with the belief they might not have the ability to maintain the momentum sooner or later – ideas ? I assume an alternative choice could be to promote a sure proportion of all shares till I hit my capital positive factors restrict for the 12 months.

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

Thanks upfront !