Here's an example of the sort of Monte Carlo equity curve resampling features provided by vendor-sold software. I've run it on an experimental mechanical system of mine (called "ZD_rev_01"), trading a global portfolio of 104 futures markets, from 01 Jan 1980 through last Friday, 31 Oct 2008.
In the top panel we see the probability density function (solid "mound") and the cumulative distribution function (curved green line) from the Monte Carlo procedure. 20,000 equity curves were generated by resampling the backtested results, and statistics were measured. 95% of those equity curves (19,000 out of 20,000) had a Compound Annual Growth Rate ("CAGR") greater than or equal to 111% per year (vertical line).
In the middle panel are the density functions and cumulative distribution functions for the Nth biggest drawdowns (N=1, 2, 3). 95% of the resampled equity curves had a Biggest(N=1) drawdown of 36.5% or less (red vertical line). And 95% of the equity curves had a 3rd-Biggest drawdown of 26.8% or less (green vertical line). The middle panel shows the "depth" of the drawdown, in percent-of-prior-peak.
Bottom panel shows the "width" (duration) of the N longest-duration drawdowns, in months. 95% of the resampled equity curves had a longest drawdown lasting 11 months or less (red vertical line).
The software also generates a number of histograms; I've attached 3 of them below. They show returns, by month and by Chuck Branscomb's R-multiples.
In the top panel, for example, we see that 41 months (out of the 346 months in the test) had monthly returns between +2% and +4%. (tallest green bar).
In the middle panel we see there were 7520 losing trades and 5899 winning trades (44% winners). 3891 of the losing trades risked R dollars at initiation, but were exited at a net loss of less than 0.5*R dollars (tallest red bar). 1240 of the winning trades risked R dollars at initiation and were exited at a net profit between +R and +2R dollars (second green bar).
Histograms like these can help you get a feel for the relative importance of big winning trades, big losing trades, small winners, and so forth.