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 primarily based by myself analysis.

Nonetheless, I’ve lastly realized that I used to be doing all of it incorrect to start with – I’d have been a lot better off in the present day had I invested usually in some low cost low value ETFs as a substitute of betting on particular person shares. Whereas a few of my shares similar to AAPL,MSFT,GOOG and so forth. appreciated considerably, just a few haven’t completed so nicely similar to DIS, BA, DAL and so forth. Total, my portfolio has appreciated however it’s positively in need of 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 preserve preserve it easy by utilizing automated investing. Nonetheless my essential dilemma right here is cope with the tax implications for such a serious transfer.

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

I just 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 internet realized long run beneficial properties of about $9k already. I’m pondering of following this technique yr over yr subsequent 5-7 years till most of my particular person inventory positions have been rebalanced into just a few index primarily based 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 beneficial properties, like most different individuals)

So the large query could be which shares ought to I promote first – those which were constantly underperforming the market or ones which have carried out nicely up to now with the idea they could not be capable to maintain the momentum sooner or later – ideas ? I assume an alternative choice could be to promote a sure share of all shares till I hit my capital beneficial properties restrict for the yr.

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

Thanks upfront !