Hi Thad!
You know, since I started this hobby in mid-May of this year, I have never actually counted how many I enter a day. I would guess my average is somewhere between 50-100. On weekdays (a few in the morning, most after work in the evening), almost without fail, I probably enter about 40-50, mostly off a list from one of my favorite freebie sites. About half of those are IW's. On weekends, I usually branch out and enter stuff like blogger sweeps or the little one-time entries offered by e-book authors (for Amazon gift cards, etc). Or I spend more time on sites like Poshly (you have to take little quizzes for each entry), or ABC Soaps in Depth (considered a "creative presentation" since these are actually offered via many portals) where you have to watch little videos before each entry (I am still not sure those are worth the time/effort though, so I try not to spend too much time there).
I also noodle around on sites like Candystand, Dial Rewards, and DailyBreak to earn and spend points on sweeps, raffles and IW's, but I usually don't spend more than about 10 minutes or so total on these. Haven't won anything from these yet, but I really only started incorporating them into my daily routine a month or so ago.
Now, a lot of the sweeps I entered are still going on, or just wrapped up recently, so it's possible I could've won something "big," but don't know it yet! I also didn't realize it when I first started, but many IW's allow you to win multiple prizes (some limit it to a certain number, or once per week or entry period, etc). There were a few I thought I had hit my limit on with my first win, but actually hadn't. It was only when I saw other folks winning multiple prizes that I went back and re-read the rules with a fine tooth comb! You'll notice the wording in the official rules can be very tricky ("per household" vs. "per email address" vs. "per week" or "per day" -- and you might be looking at the ENTRY limits vs. the PRIZE limits -- and/or the limits on various prizes can be different in one sweeps, i.e. "grand prizes" vs. "game prizes"!)
Another tip is that I avoid entering anything I'm not interested in or doesn't apply to me (even if I'm technically eligible). I'm not a parent, so I avoid anything kid-related. Some things I entered early on that I realized had so few things that appealed to me, I dropped out. On the other hand, some sweeps that I thought would be too time-consuming turned out to be easier than I thought (or I enter them when I have more free time), or had a way to skip what seemed like a required step (i.e. Nathan's Famous Selfie sweeps -- you can enter the IW without submitting a photo). I also learned, through these boards, you can almost always skip having to play any of the games and get right to the entry screen (though some are trickier than others to locate -- i.e. with the Nabisco Race game IW, I figured out you have to hit "Let's Race," pick a car, and only THEN you'll see a link that says "Skip the Race.")
As other long-time sweepers have said, patience and persistence pays off! I have a little notebook that has all my daily to-dos in it, and every morning I start a new list with everything I want to get done. About half of my list is devoted to keeping me on track with my entries! When I start feeling burnt out or discouraged, I jump on the SA forums, or read contest blogs, or just watch something on Netflix! I also rack up points on sites like Swagbucks to earn gift cards, so even if I don't win, I've still got goodies coming in! It will be interesting now that I'm unemployed (officially as of Tuesday). I'm hoping I can expand my hobby in between my job search. Wish me luck!
I'd love to hear more about your daily strategy, Thad!

Hang in there!!