I have a similar situation to you in that I have a few hundred diverse options within an hour of where I live, the majority of which are small (a few hundred acres or less). I battle a weird and irrational sort of decision paralysis, where it feels wrong to select any one place to fish, because then it means not selecting all the other places I want to fish. That's ridiculous of course, but if you experience the same thing, you know what i'm talking about.
My solution has been to plan my seasons ahead of time by creating a fishing schedule of the places i plan to go, and when I want to go there. I do this over the winter to create a month-by-month breakdown of where I will plan to go, when I will go there, and how many times.
Start by picking a diverse selection of locations you want to fish over the next several months, or season or year or whatever -- pick a few favorites you've been too a lot before, pick some you're a little familiar with, but would like to get to know better, and pick some new ones you want to try for the first time.
Then put together a loose schedule based on when and how often you plan to fish each one you have picked for your schedule. In my case "loose" means each month has a number of locations I want to go to, with an order of priority and a rough judgment when in the month I should go ('early" or "late"). Use the characteristics of the various water-bodies (e.g., water levels, weed growth, etc.), local event schedules (e.g., tournament activity, holiday parties), and seasonal information (e.g., pre-spawn, post-spawn, summer, fall) to help anticipate when would be best times to hit each of the places you want to target, and when would be the best time to avoid them.
For instance, In the prespawn season, I can anticipate that smaller, shallower, dark-bottomed waters in my area will warm up faster than bigger, deeper ones, so I put the former on my schedule first, and then move to the latter as a the spawn progresses. I also usually put river float trips on the schedule for july and august when the lake bite gets tougher, but the rivers are running low and clear and the bass will be concentrated in predictable areas.
And there's nothing wrong with choosing at random either, especially if you can't think of any better reasons to pick one option over another. The point is just to get the decision made, so you can promptly move on to the task of showing up and figuring them out.
This also permits me to be systematic about exploring and learning various water bodies. If I have been to a lake, say, twice before, but both times were in May, then I put it on the schedule for a different month the next time I go, so I can sample locations at different times of the year.
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