I set six lineups yesterday, not including the RotoWire and Tout Wars contests - more on those below, for an outlay of of $20 (five $3 ones and a $5 one.) I cashed in two for a total of $14, meaning I had a net loss of $6. My bankroll was at $961.60, now it's down to $955.60 (following this blog is like sweating a 2/4 limit game, I know.)
That said, I actually won $90 on the Rotowire (16 out of 424) and Tout Wars (1 out of 50) contests . Those count toward my real-life bankroll and sense of self worth, but not for purposes of this blog because they're freerolls to which most people don't have access. But I mention them because they're lineups I'm setting and for which I'm getting results that are informing my evolving DFS strategy.
At this point, I'm inclined to blanket the $3 or $5 large-field tournaments with multiple entries, using 2-4 pitchers and matching them up with stacks I can afford. Some stacks are obvious - lefties against Justin Masterson, for example, and others less so - Brewers against Bartolo Colon last night or Blue Jays against Dallas Keuchel. Unless the tournament had a million entrants, I doubt I'd ever stack against a top-10 pitcher, but I think there's an advantage to targeting pitchers running well as most people won't want to mess with them.
The other key is choosing pitchers. On FanDuel - especially with the softer hitter prices - I'm often inclined to go with the chalk, e.g., Clayton Kershaw last night in a few lineups, because now you can still afford decent, high-in-the-lineup hitters. I'll also throw in a couple cheaper options based on matchup, park, Vegas odds and gut instinct.
I also tend to like good pitchers who have fared poorly in recent outings without losing velocity. For example, assuming he makes his next start, I'll probably be on Stephen Strasburg even if he's expensive. Not only is his percentage-owned likely to be inversely correlated with his price (meaning you either get a discount or a lesser-used player), but my hunch is when great players fix their mechanics or whatever the issue was, you'll often see them at their best initially. Then over time, like a car whose steering gradually goes out of alignment, they can stray before the next adjustment. While you never know which start is the one where the pitcher figures it out, it usually doesn't take more than a handful for the top players. That's my theory at least.