Simulate a portfolio of investments over a multiyear period

You plan to simulate a portfolio of investments over a multiyear period, so for each investment (which could be a particular stock or bond, for example), you need to simulate the change in its value for each of the years.

How would you simulate these changes in a realistic way? Would you base it on historical data?

What about correlations? Do you think the changes for different investments in a particular year would be correlated? Do you think changes for a particular investment in different years would be correlated? Do you think correlations would play a significant role in your simulation in terms of realism?