Hey Tim,
I like Mavericks, either the ET-732 or 733. The 735 has Bluetooth, but seems to be having "new model" growing pain issues - I'd wait a bit on that one. Just drop the probes through the top vent hole (I call it the "blow hole") - no need to drill any holes! Yes, clean the probes with each use, just be sure to not submerge them in water, or you'll ruin them. One thing I like to do with new probes is to add a little high-temp RTV sealant around the top, where the wire enters the probe. This will help moisture from getting inside, and make them last a lot longer.
If you ever go with a controller like the Auber PID, you'll have meat and box probes built-in, so you won't need a separate thermometer.