here is my personal experience:
I've used outreg and then outreg2 for a number of years. Outreg2 is the easiest to learn. It meets our needs most of the times. except the following situations:
1. suppose you want to have an LR test or chow test, et al. and include the test results in the table, it's easier to use estout.
2. suppose you want to include AIC, BIC results, it's easier to use estout.
estout is more powerful and more flexible. it can do everything that outreg2 does and more. but it takes tons of time to learn and get familiar with estout.
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