Gotta do some thru-hull work, advice? (lights, temp sensor)

2007 246 Cuddy
I bought a blue underwater LED to put on the transom, but where?  Under the swim platform would be easiest but out of the water - anybody ever put a light shining down, AT the water but not in it?  (I realize this is probably the least important question ever asked on this forum ) :-)
Also have a seawater temp probe to install.  Would really like some advice on drilling techniques, placement, sealant methods, sealant products, etc.  Planning to do all with boat in the water. HA! just seeing if you are paying attention...
Thanks in advance

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