Thanks Monty, but I am hardly an expert (trying to be though, give me a few octo years/generations)
Simple,
Sometimes DanTheMarineMan (TONMO name) has a collection of them available. From Mid-December through about March they are often plentiful because of the stone crab run (the get into the crab traps). My best recommendation from the little I have learned is to look for one with the fattest, biggest body. Sometimes females will lay eggs in their holding cup at a collection facility and you can acquire the mother and eggs. Most collectors are small, family run businesses and you can dialog with them about what you want. You may not get it "tomorrow" but you have a better chance of obtaining a female this way. Another sign is to look for an enlarged sucker at the base (nearest the mantle) of at least three of the front legs. This will be a male and the sucker is about twice the size of the next largest (my best guess is it is for mating). If you acquire a WC adult female, the chances are very high that she will have mated (particularly late in the year). Octos can mate multiple times and will store the sperm separate from the eggs until the female is ready to brood. Trapper was with me for three months before she brooded her eggs. She had an extremely small brood. Her offspring, Miss Broody, mated one week and has isolated herself ever since so I think she will produce eggs shortly (or already has). There is no scientific approach to dealing with reclusive wild caught octos but these are my best thoughts. If you can view the octos available from your collector, pick out the largest one. My males seem to be smaller than my known female (I have two that I am not sure about their sex because I can't get a good look at them) and her enlarged mantle made me aware that she was manufacturing eggs even before she mated.
Yes, there is a risk of problems mating sibblings but what the risk is is unknown. Ideally, you would acquire two pregnant females and attempt to pair the separate broods. This would mean trying to raise roughtly 200 octo fry and separating them into pairs (or at least separating out the females) at the point of suspected sexual maturity. Even though you may keep multiples in a single tank, you can't keep a great number (three in my 45 seems to work but one is only seen once about every two weeks). Even dealing with 100 will be expensive and difficult. If you live close to the ocean (the one where the octos came from only) you can release some of the fry to minimize the numbers but the cost and time are still high. If you are expecting to make a profit, I fear you are in for a disappointment. The adventure is well worth it but the financial and time costs are high.
Whatever approach you take and whatever the outcome, please start a journal on the adventure.
If Roy Caldwell (who really is an expert) happens to read this post, he may be able to offer some insite about problems with sibbling pairings. I am mulling over what to do if my sibblings produce healthy young but am thinking and waiting to see what transpires over the next couple of months.