This has been a good read. I have another point of view that I would like to share if you don't mind.
I found WIS a little over a year ago in an ad on BBR. I had never played an online-based sim sports game, having only played simulations on EA Sports video games. I first tried experimenting with dream teams and pitting them against the active teams with the best winning percentages in practice games, not knowing that some of those teams were theme league teams with limitations. I then tried a spring training and then an OL and made the playoffs. But I too did not understand the dominance of Joss or why Schilling bombed so badly. Not wanting to face Joss again I chose to try a few theme leagues, where I promptly got my butt handed to me. Eventually I made the playoffs again but it wasn't until I started reading the forums and getting some advice from certain HOFer's here that I started to understand how the normalization worked (and still have lots to learn).
I have only played in 2 OL's in my WIS career but what I have noticed about it both times is they are not very friendly places to be a newbie. Not just getting beat but even posting in the league's owner forum. I tried to banter around but when you're comments get completely ignored by everyone, it doesn't make you feel much at home. Or comfortable asking for advice. Mostly, the banter (when there was some) was about the Joss haters hating on the owners who drafted Joss. Although this is good advice when you are a newbie, it is also the first thing you learn (albeit not understand) in WIS, that Joss is godlike in this game.
Personally, after learning how the normalization works AND accepting it for what it is, I think the SIM is alot of fun. It helps when you play with some of the same owners to build relationships that will make a newer owner feel comfortable, something that doesn't happen in OL. And i have been fortunate enough to play in some of these leagues.
I agree with alot of what has been said here in regards to WIS management but I tend to try and focus on the things I can control and WIS management is not one of them. But one thing the patrons of WIS can control is how welcome newbies feel in a league. Sure you HOF'ers are getting yours by beating the crap out of unwitting newb's but if you want them to stay at WIS, maybe it would be a good idea to initiate conversation with the poor sap and offer up some pointers. Or when one starts crying in disbelief about Joss, don't ignore them but offer some assistance on strategies to beat him. Give them a little insight on how the game works and what some of the nuances are. We don't have to be totally dependant on WIS management to educate newbies on the intricacies of the SIM. Then at least the newbie has an idea of what he should do next. And feels a little more comfortable in asking advice. Sometimes a little encouragement is all that is needed to keep a new owner hungry and interested.
Well, that's my two cent addition.