Pull Random Numbers from my Data (Python)
If what you want is to generate random numbers with the same distribution as your cashflow numbers I recommend you using Python's Fitter package
It is powerful and very simple to use.
You can in this way use it to find the distribution of your data and then generate random numbers with the same distribution.
From documentation:
from scipy import stats
data = stats.gamma.rvs(2, loc=1.5, scale=2, size=10000)

from fitter import Fitter
f = Fitter(data)
f.fit()
# may take some time since by default, all distributions are tried
# but you call manually provide a smaller set of distributions
f.summary()

Also useful resources might be found in stackoverflow