Does my Electrum wallet become less secure if I keep generating seeds until I see one I like the look of? Let's say I want to create a new electrum seed... I didn't like the initial seed words, since I want to remember them and these didn't look too appealing. Looking "too random" for my taste. When I repeat this process like 100 times, chances are that I like the combination then more, because it looks "less random" or "more logical to me" (looking like a short story being summarized) which is easier to remember.

Is doing this insecure? Do I increase my risk of randomly creating a not-so-random seed by redoing the seed creation until I get a seed that I like?
Yes, this does reduce your security. The fact that the seed words were generated randomly becomes meaningless if you use a non-random process to select the seed that you actually use. For instance, it is entirely possible (though very unlikely) that a random password generator would generate a phrase such as "Columbus sailed the ocean blue in 1492". You might say gee, what luck - that is a great password to remember, I'll use that one. Yet, a password cracker that tries meaningful phrases before moving on to random strings will be able to crack this password in the initial phase, even though the probability of randomly generating such a phrase is the same as for any other character string of the same length.