Real Estate or Stocks. Same ROI, Which is Better For Taxes?

[William Coet]

If a RE investment and Stock investment return the same amount of ROI over a 15 year period and then sold which is the better investment? Assuming a 1031 is not used (they may not exist in 15 years), do certain structures of owning the stock (Roth ira) make the stock investment more desirable from a tax perspective?

Thanks!

[Christopher Smith]

I use a variation on Buffett's strategy to avoid paying any meaningful tax on my stock portfolio.

1) I invest primarily in high growth stocks and ETFs so currently taxable dividends are minimized.

2) I only invest in securities I intend to hold indefinitely so currently taxable capital gains are minimized. Losses on the other hand can be currently harvested to benefit from the loss deduction. Since I'm exceedingly selective upfront because I intend to hold all my stocks indefinitely my losses have been very few and far between.

3) All the capital appreciation on my stocks will be wiped out in my estate so my lifetime taxes paid will be negligible.

4) A Roth works too, however I don't qualify and conversion of my regular IRA would be tax cost prohibitive.

5) All my current and future cash needs are funded from RE portfolio and work. RE portfolio also allows me to cash fund additional stock investments with significant pre tax money (i.e., the depreciation sheltered component).