Here's what my bankroll strategy has evolved into.
I enter contests early in the week, but save some GPP money for the contest lock to see if I can find some overlays. I don't usually find many.
All percentages are of the money I'm willing to put in play for the week.
80% to cash, 20% to GPP.
All the money is split evenly between THU-MON and SUN-MON, so 40% cash starting THU, 40% cash starting SUN, 10% GPP starting THU, 10% GPP starting SUN.
Of the 80% towards cash, I put 10% (so 8% of my total money in play) of that towards 1 H2H THU lineup, 10% towards 1 H2H SUN lineup. These lineups usually look pretty similar. I try to avoid negative correlation. I target for users with not many entries, sometimes look up the users, or just make my own entries and set it so I don't play the same user in every matchup. I mostly enter $1 and $2 contests.
Then, I have three more cash lineups for each of the two primary slates (i.e. starting THU and starting SUN). The amount I put towards each lineup varies depending on how confident I am with it, but for each lineup I put 50% of the lineups budget towards X2, 30% towards X3, and 20% towards X5. I usually target double-ups with large player pools, while I target triple-ups and quintuple-ups with smaller pools. My rosters usually have a player stack in each of them.
For GPPs, I put each of my already made rosters into a game, and then make a #### ton more to get exposure to some players I've faded so far, and some lesser owned players. If I get to a point where I feel like I'm getting diminishing returns or just throwing darts, I enter more cash games with lineups I'm more comfortable with, or enter some of the other slates.
So far I've turned $25 week 1 into $400. Pretty happy with what I've done so far. I'm risking pretty much all of my money each week, but trying to mitigate the risk by sound bankroll management and making sure I have decent exposure to a variety of players.