I am interested in a couple of points around this:

What makes this worse is that the region of 0.05% to 1% of my net worth is full of long tails. The wagers I’m skipping could easily repay themselves a thousandfold. If I take a wager like this every day for 2 years and just a single one of them repays itself a thousandfold then I win bigtime.

If I take b = 1000 and f* at 0.0005 I get p ~= 0.0015

If I take b = 1000 and f* at 0.01 I get p ~= 0.011

You draw from this the lesson that you need to bet more. What do you see as a source of potential wagers, coming along daily, where there’s a potential 1000x payout and your probability of a win is between around 0.15% and 1.1%?

Also, I’d urge caution over the “[if] just a single one of them repays itself a thousandfold then I win bigtime” framing.

At the p=1.1% / bet=1% of wealth situation, one win in 730 (daily for 2 years) would take a starting balance of $100,000 down to $718. Now, treating this as binomial distribution, that’ll only happen 0.25% of the time, but 2 wins leaving you with $7,990 will happen 1% of the time and 3 wins, leaving $88,871 will happen 2.8% of the time (assuming I’ve not mangled my calculations).

(Yes, in ~96% of cases you’d be left with $988,451 or greater, typically much greater, in the $millions, $billions or $trillions. But this is a caution against thinking ‘only one of these 1% chances in 2 years has to come off to be winning bigtime’.)

At the other end of the spectrum you mention, i.e. the bets are all at the 0.05% of wealth (p=0.15%) situation, the results are much less dramatic.

wins=0, closing balance = $69,337 (prob = 0.33)

wins=1, closing balance = $104,162 (prob = 0.37)

wins=2, closing balance = $156,478 (prob = 0.20)

wins=3, closing balance = $235,070 (prob = 0.07)

wins=4, closing balance = $353,134 (prob = 0.02)

Maybe ‘Private Eye’ in the UK might have some parallels.