I'm not sure which one is best to sight-read. I would prefer the second measure because there are fewer notes to read, but I know that you can see where the beat lands on measure one.
As a general rule of thumb, you want to be able to see the beats. I would prefer number one for that reason. Sure, once I've figured it out, either is fine. But the first is easier to sight read.
As an aside, less notes is not necessarily easier to read. Double dotted notes are a good example. I haven't ever encountered a double dotted note that made the rhythm more legible.
If you're taking your time, and reading it to learn it, maybe the fewer notes the better. But, reading it cold and having to get it right first time it helps a lot to see where the main beats in a bar are. Minimum would be beats 1 and 3 - the bar 'divided into two', but seeing all four is easier to read - and the ties make that clearer: here, the last beat is 'pushed' in the first example.
More and more music is written without that tenet in mind, but maybe that's in the printing process, and thus is dependent on how it's programmed on computers, but I don't see that as a forward step. The idea of writing stuff out is for others to play and enjoy, so the simpler and easier should win every time.
I personally would find double-dotted notes perfect in this situation. A sixteenth plus double-dotted quarter is the textbook equivalent of a half-note: no ambiguity there. It would also eliminate the need for a double tie. You would then tie the double-dotted sixteenth to the first sixteenth on beat 3 like and end with a dotted quarter, like you did in the second bar.
I suspect that you may get different answers from classical versus jazz musicians.
I'm torn a bit on this. Measure 1 is easier to interpret where the beat falls by reading it. But, it doesn't do much in the way of helping me understand the feel nor does it make it easy to learn the rhythm by subdividing. Meanwhile, measure 2 allows me to near-instantly learn the rhythm with an easy subdivision, however, it would be internalized as a "felt" rhythm rather than a "read" rhythm, if that makes any sense.
I think in the end, it's better for personal development to go for measure 1.