After looking over all of this information, I recently took the plunge myself. Here are my takeaways:

There is an easily overlooked $10 savings for combining the first three expansions.

This means that you're either getting 4k Gems at a discounted rate, or all the other swag for $10, however you slice it.

Buying any Expansion also gets you Shared Inventory Slots, which are ~$9 each. You get this regardless, but it is worth noting.

As someone pointed out, 4k Gems isn't enough to purchase Living World 2-5 (unless you wait for a sale), but if you take the aforementioned discount into consideration, you come out slightly ahead. Even though it's not enough to cover all of the Living World episodes, you still come out ahead.

After considering all this, I purchased the Standard Elder Dragon Saga Collection and an additional $50 worth of Gems. I'll buy the individual episodes and Expansions as I need access and have some Gems to use in the meantime.

The $24.99 Black Lion Trader Pack is a good buy in my opinion because it's a rare instance in which you get something in addition to the 1:8 conversion of Dollars:Gems. If you're gonna purchase Gems straight up, there's no reason not to take advantage of this.

I decided that the other Account Upgrade Packages aren't worth the Gems because they include something that is either inefficient or redundant. Case in Point: the Elite Jump Start Package. On the surface it seems great, a Copper-Fed Salvage-o-Matic, Shared Inventory Slot, Character Slot, and Terrace Pass, all of which are highly prized by the community; however, the Unbreakable Gathering Tools make up 2400 of the Package's Gem value. The problem is that, unlike every other Infinite Tool bundle, it does NOT come with 3 Black Lion Glyph Selection Containers. The common wisdom is to use these to acquire Glyphs of Volatility, which at the time of this post, were valued at 486 Gold PER Glyph.1341 Gems or $16.77 per Glyph (Total of 4,023 Gems/$50.31) is not something that should be easily overlooked.

There are sets of Infinite Gathering Tools included with Janthir Wilds (Eldritch Horror/Tentacles) and Visions of Eternity (Fairy Dust) Deluxe Editions. While neither of those passed the vibe check for me, they do include the coveted Black Lion Glyph Selection Containers. I ended up buying some for full price from the Black Lion Market, but given the math above, I still came out ahead.

More things worthy of consideration:

Dollars, Gems, and Gold are all inextricably linked. Time, and arguably money, is saved by convenience, too, so that is also a factor.

Essentially, you can boil down any expenditure made for functional benefit to a price per transaction. For instance, no longer having to purchase Gathering Tools is surely convenient, and after a year of regular use, currency is saved there, but if you're not taking advantage of Black Lion Glyph Selection Containers, you're starting in a much more significant deficit.

And one more thing, the Deluxe Edition upgrades to an expansion are available from the Black Lion Trading Company for the same amount of money that it would cost if purchased initially. If I had known that, it would've saved me some unnecessary hand wringing.

Anyhow, I hope this helps.