Hello there!
Please keep in mind that you and I both know I am not a professional; my suggestions are just that, suggestions. In the end, do what you feel is right for you and your writing! Any suggestion I make is simply given out of love for words, literature, and writers/creators, and a desire to simply help you become the best writer you can be.
We are both participants in the "I Write 2019" activity in WdC. My week 3 entry is posted just after your post, so this is what brought me to your work and this review.
Introductory Lines/Stanza -- Hook:
There were several different 'hooks' for me initially.
I think that by rhyming lines 1 & 2, you created an attractive 'sound' in my head. Also, your references to "a new vantage point", "images coalesce", "new horizon's formed", "challenges", and "bright new lands" all definitely kept me reading.
When I scanned up and down, the reference to WdC and your development as a writer, I was hooked even more.
Another hook was the fact that you chose to complete an item for this contest. I occasionally submit to this one too, but the Sestina proved to be a bit daunting and I ended up putting time and effort into other writings in the days leading up to the Taboo Words deadline for that round.
Looking back, your first line also 'hooked' me. That question is compelling, plus you did a wonderful job of walking us through the subsequent years along with your growth and WdC's impact. I really liked that as I can strongly relate! 
Rhythm / Format / Rhyme Scheme / Meter / Poetic Traits - -
Above, I already shared that I find this format a bit challenging.
You put a lot into this, and the efforts paid off. It is full of meaning and ripe with literary elements (that I'll detail below).
For the format, I did see one error. This is the 'formula' I found in my research:
1 2 3 4 5 6
6 1 5 2 4 3
3 6 4 1 2 5
5 3 2 6 1 4
4 5 1 3 6 2
2 4 6 5 3 1
(6 2) (1 4) (5 3)
I found that in stanza 4 you did not include the word you're using for #4, "high". It looks like you accidentally used the word "point" twice. IF the information I have for this format is accurate, then you'd want to make the appropriate change there.
Also, in my research, it looked like the final stanza should have the words 6 & 2, then 1 & 4, then 5 & 3 in the 3-lined closing stanza. It looks like your pieces includes (2 1) (4 3) (6 5). If that's the design for a different version of Sestina, then no worries. Otherwise . . . FYI.
Imagery / Figurative Language / Etc. - -
I adore figurative language and your piece provided a feast! Here are a few snipets that I especially enjoyed:
imagery (visual, paint a picture mind movie) - - "seems to fly ... when memory's wings spread, lifting me high," - "a new vantage point" - "images coalesce" - "new horizon's formed" - "bright new lands" - "allow my spirit to fly' - "barren regions" - "rediscovered the sweeping vista of lands / that could only be seen from on high." - "my new wings carried me and I could fly." -
metaphor - - "a community of words"
personification - - "memory's wings" - "allow my spirit to fly" -
simile - - "Like Icarus," - "spread their beauty, like seeds, to new lands." -
allusion (mythological) - - "Like Icarus,"
alliteration - - "not fully formed." - "confidence came" - ("a stranger in strange lands") (repetition) - "convinced me I could" - "from point to point" (repetition) - "whispering words"
Examples of Favorite Phrases and Word Choice - -
"seeking asylum in a community of words"
"They cajoled, ganged up on, and dared me to fly"
"As though engraved, chiseled words / of strength convinced me I could fly"
"heir wings stunted and unable to fly."
"Within these sheltering lands, new wings have been formed."
" that only upward point."
Actually, you could add each of the examples of figurative language listed above here also since for me they are so enjoyable!
Resolution - -
Strong! Following along year by year and proceeding through, this is strong and logical, but also meaningful. The outcome is positive an pleasing after learning of your journey and some bumps in the road.
Room for improvement - -
So little!
Just, I think (if my research on format is correct), the two items about the placement of a couple of the words.
I only noticed this after scanning my notes above, NOT as I was reading, but it appears that the imagery you included is primarily visual. Additions of the sense of sound, smell, etc. might be a consideration, but it's such a strong piece already that maybe that's just an option to "file away" for other future pieces.
Final note - I also liked your cover image! It fit SO well! I see that many writers don't do much with these images, but I find them fun. I try to put thought and effort into them. To me, as I look through my portfolio, the image represents the piece and holds meaning. I appreciated the significance of this in your posting.
Thank you for sharing this piece. This obviously comes from the heart, and it touches similar experiences/memories/places for your readers also.
Well done!
Ruth Rodgers (RRodgersWrites)
** Image ID #2123092 Unavailable **
 
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3 - Sentence 2 - This reminded me of the studies done on laughter & endorphins. They had patients watch comedies and laugh a lot, while their control groups watched dramas or other genres, and indeed the laughter group fared better! 
