Because I can fit e.g. ~25 distributions via empirical cumulative distribution fitting to correlated data (including stable dist.), and then simulate the original data based on correlation (covariance) using the best fitting distribution for each feature, I am planning on the following three approaches regarding MC and bootstrapping for estimating optimal weights for monthly re-balancing (20 trading days).
PROPOSED MONTE CARLO APPROACH
Fetch about 2-4 years of daily price data for the stocks of interest, estimate log-returns, and fit various distributions to the log-returns for each asset. Then, using the correlation between the assets, simulate small blocks of e.g. 20 days (1 month) of log-returns.
Next, use MV minimization (tangency portfolio) with the mean returns and covariance matrix for the 20-day sequence of simulated log-returns, repeat $B=500$ times, and average the weight vectors $\mathbf{w}^{(b)}$, portfolio returns $r_P^{(b)}$ and portfolio variance $\sigma^{2 (b)}_P$ for all the $B$ iterations. Determine the median, and 10th and 90th percentiles of each ($\mathbf{w}$, $r_P$, $\sigma^2_P)$.
RANDOM WALK-FORWARD (BLOCK SAMPLING)
In the nice paper by Daly et al on covariance noise filtering via Marcenko-Pastur and daily data, they randomly selected test dates and used data for the following 20 days as the data for each block. During each iteration, all data prior to the randomly selected test date were used for the in-sample training data, and separate analyses were done on the out-of-bag data. They basically filtered covariance and correlation matrices for the training and test (20-day block) data and reported the number of signal eigenvalues greater than $\lambda_+$.
My thoughts here would be to simply generate the return vector and covariance matrix for each 20-day block (of log-returns), and then use MV minimization via a tangency portfolio for the block. Repeat $B=500$ times. This approach would conserve between-asset correlation while also using the observed mean returns, which are alternate realizations.
PURE BOOTSTRAPPING APPROACH
This approach would involve simply fetching random daily data (selecting one day at a time) to construct sequences of e.g. 20 days, which would then be MV-minimized for a min-variance (not tangency) $GMV$ portfolio, assuming zero mean returns, since any information related to mean return here would be biased and false, as individual days were randomly sampled. Repeat $B=500$ times.
I think all three methods above have merit, since the first simulates correlated returns for small sequences of data and applies a tangency portfolio. The second method randomly fetches blocks of data and generates tangency portfolios for each. The last approach simply fetches random days to construct 20-day sequences, and assumes zero returns for the $GMV$ portfolio.
In light of the above and the numerous ways in which MC can be applied to portfolio optimization, which approach is more common for determining weights to be applied during a monthly (20-day) re-balance?