darkhorse,
<b>Bootstrapping</b>
Your bootstrapping concept (using our own money to get a foot in the door and then only use the market's money after that) sounds very intriguing. The tricky key to bootstrapping, though, is to ensure that one's very first trades are winners. A drawdown at the very beginning puts he trader "in the hole" and trading on their own capital until they get back to break-even. Hmmm.. perhaps traders would want to use a split trading strategy -- trade their own money using a conservative, high P(Win) strategy and trade "the market's money" with a high-margin, high expected return strategy.
<b>When Margin has Low Utility</b>
Me, I'm more partial to thinking in terms of utility functions as a means of thinking about the actual value or danger of accepting risk (although I admit that I cannot quite pin-down my own personal utility function, I do know that I am risk averse). One common risk-averse utility function is U(V) = ln(V), which is the natural log of the dollar value of the account after the trade and U(V) is the utility assigned to that outcome. This utility function displays constant relative risk aversion and would have the trader invest a constant percentage of assets in risky endeavours, regardless of wealth level. Thus U(V) = ln(V) jives with the common trading advice of risking a constant 2% or so on each trade.
To give an example, a person with this utility function would accept a 50:50 bet in which they lose 1/2 of their trading capital with a chance of 50% or double their trading capital with a chance of 50%. Note that the dollar expectation on this bet is strongly positive and reflects the risk premium that this risk-averse trader demands. For very small wins and losses, this utility function is nearly linear -- the person would be indifferent to a 50-50 bet with outcomes of 2% loss vs. 2.04082% win. (Of course this utility function also implies that the trader would accept a 50:50 bet that gave either a 95% drawndown(YIKES!) or a 20X increase in the account (WOOHOO!). OK, maybe I'm more risk averse than this "risk averse" utility function implies.

)
Anyway, when I rerun the sims using this utility function, the expected utility of trading with margin has very different properties. A person with this type of risk aversion would have some optimal margin level (i.e., excessive margin has negative utility because the high chance of ruin outweighs the the slim chance of lottery-like winnings). With a bit'o analytic work, one can show that a binomially distributed trading system has an optimal margin level of:
Optimal Margin = -(Pwin*Dwin + Ploss*Dloss)/(Dwin*Dloss) where:
Pwin = the probability of a winning trade
Dwin = the positive delta-% for a win
Ploss = the probability of a losing trade (Ploss = 1 - Pwin)
Dloss = the negative delta-% for a loss (e.g., Dloss = -0.02 if we risk 2% loss)
Notice that the numerator is just the expected return for the trading system and that the negative value of Dloss in the denominator corrects the negative sign on the equation to give a positive value of optimal m. Note also, that m can be any positive number for a trading system with positive expected return. If m > 1, then the optimal strategy for a risk averse trader (who obeys the U = ln(V) utility function) is to borrow margin at a rate of m:1. If 0 < m < 1, then the optimal strategy is to only devote only a fraction of trading capital on any one trade. Note also that this formula is restricted to cases where m < -1/Dloss -- i.e. it does NOT apply to extreme combinations of over-leverage and excessive loss that can leave the trader with a negative account value (the U = ln(V) utility function means that the risk averse trader will avoid this case at all costs).
<b>BIG DISCLAIMER</b> This "optimal m" still carries with it a distinct possibility of very nasty drawdowns (the utility = ln(V) is not completely risk-avoiding and will accept arbitrarily large drawdowns if the chance of extremely large winnings is large enough). And this optimal m still has ALL of the problems mentioned in the "Ugly Issues" list of my previous posting. Furthermore, this formulation assumes that the trading system obeys the simple statistical model of binomially distributed returns (wins and losses always have exactly the stated returns with exactly the stated probability with no correlation between successive trades). YOUR MILEAGE MAY VARY, but at least this formulation of a risk-averse value for optimal margin under a set of assumptions gives one some idea of how much margin to use.
OK, now my head hurts,
-Traden4Alpha