In general, more data is better than less data.
On the topic of your specific scenario, you want to cluster by date or use some other procedure to produce consistent standard errors in the presence of cross-sectional correlation.
Monthly returns are basically uncorrelated over time but exhibit significant cross-sectional correlation.
With large quantities of data, treating correlated error terms as uncorrelated can massively understate standard errors!
Example:
Let's say I have $i=1,\ldots,50$ people recording the results of me flipping a coin 20 times ($t=1,\ldots,20$). Let $y_{it}$ be person $i$'s recorded result of flip $t$. I have $20 \cdot 50 = 1000$ observations.
My model is:
$$ y_{it} = \mu + \epsilon_{it}$$
If I treat each $\epsilon_{it}$ as uncorrelated, I'm going to massively understate my standard errors. In reality, I have basically 20 independent observations, not 1,000. For each time $t$, the $\epsilon_{it}$ will be significantly correlated.
Basically the same thing happens with returns
For any time period $t$, returns ${R}_{it}$ are correlated. There's huge cross-sectional correlation.
Hence, you'd want to cluster by date. There are other methods of course to deal with cross-sectional correlation.
The same logic is behind:
- forming portfolios and using time-series variation in portfolio returns
- the Fama-Macbeth procedure of running $T$ cross-sectional correlations and taking the time-series average and standard deviation to compute estimates and standard errors.