How to win a super-deep fantasy baseball league

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A standard fantasy league consists of 12 teams with the following roster construction:

1 C, 1 1B, 1 2B, 1 SS, 1 3B, 3 OF, 2 UTIL, 2 SP, 2 RP, 3 P, 5 BENCH

While simple and conventional, as owners gain more experience with fantasy baseball, they'll naturally begin looking for more creative ways to play the game and attempt to up the level of difficulty. Increasing the quality of competition is a simple way to do this, but not always possible when the foremost desire is often to play against friends.

Increasing the number of teams in the league and thus expanding the player pool can lead to many more challenges and a more fun fantasy baseball experience. League commissioners can also contemplate increasing roster sizes with the addition of a second catcher spot, middle and corner infield spots, and a fourth outfield spot.

All of these moves can make leagues much more competitive and fun, but they require vastly different strategies both at the draft and during the season than conventional, standard leagues.

The Draft

• Draft position matters: There are many different strategies for which draft position is ideal in every format, with personal preference always being the biggest factor. I personally have long valued a spot at one of the ends of the draft, as it allows me to select a player I need and the one I want with my second pick.
  
  Regardless of where you draft in a deep league, you'll always need to make both picks with positional and statistical scarcity in mind. Have a good eye for what talent is most likely to get back to you for your next turn. Spots in the middle of drafts decrease the wait time between picks and allow owners to get involved on positional runs before they end.

• ADPs don't: While average draft positions serve as a rough guide for where players should be drafted in standard leagues, deeper leagues are much more prone to positional runs. With upward of 16 teams involved, the talent level at each of the fantasy positions is emphasized. This will lead to more and longer runs on the positions with the thinnest talent pools.
  
  It's often more important to throw away your ADP lists and jump into a positional run before the pool becomes too depleted. Drafting the 1B8 over the C2 is much more valuable than drafting the C2 and 1B14.

• Treat it as a keeper league: Any available bench spots at the end of a draft should be filled with top young prospects not starting the year in the majors. These players will cost a premium on waivers once they're promoted, and their talent can fetch a premium via trade at the mid-point of the fantasy season.
  
  They need to do little more than outproduce the standard replacement-level players who go in the final rounds of deep drafts.

Waivers

• Always over react: Hot streaks are a common trap in standard leagues where owners give up on a superior talent when buying into an unsustainable run of production. These streaks are more valuable in deeper leagues, as these runs -- regardless of their length -- can often be more valuable than the production being provided players on the bottom half of your roster.
  
  Alternatively, any unjustifiable slump from an unproven player can warrant a drop if there is more production available on the waiver wire.

• Increase FAAB bids: Additional teams means additional FAAB dollars to go around. With the league having total money to bid on free agents, the winning bids are likely to be much higher than in standard leagues. While this will likely limit the number of total moves you'll be able to make over the course of the season, it can still be valuable to win those early bids on the first names to pop up.
  
  More on FAAB leagues can be read here.

• Get a jump on important dates of the season: As mentioned above, as soon as a top prospect is called up to the majors his value sky rockets. This will lead to much higher FAAB bids than will be required a few weeks or days before his promotion. Additionally, you can skip out on the whole waiver process altogether by making your claim early.
  
  The same goes for the non-waiver trade deadline, where paying close attention to rumors and noted available names can allow owners to acquire a player likely to go from a bottom feeder to a contender.

Trades

• Be more active: Deep-league waiver wires will be reminiscent of post-apocalyptic wastelands by the middle of the fantasy season, if not before. This puts an emphasis on trades for talent acquisition. Trade from any position of relative depth to address your team needs and be prepared to have to give up the better overall player if you're addressing a hole caused by injury.