Keaton Ross we actually used both. The first few days we did progress bar with free gift option giving customers 2 choices (using script editor to discount the price) and on giving Tuesday we used Gift with Purchase and set the tiered progress bar as decorative.
Regarding the tiered progress bar, I tested this myself and left an item in my cart both on my phone and on my PC browser. In one instance I left the checkout open, in another instance I closed out the browser completely and shut down my PC. When I went back the next day both items were still in my cart. At the same time I would add items and the free gift options for that day would also get added to the cart, so I now had 2 free items in my cart. We also tested this with EG Auto Add to Cart app and the items were removed after the free gift expired, so I still don't see this as a Shopify limitation. All these apps and solutions are built FOR Shopify and not the other way around.
And regarding GWP, yes that is correct. We gave away gift cards based on how much someone spent, and these would still be in their cart days later after the offer expired but in this case we didn't really care.
We ran into various different "issues" during this timeframe. We had different daily offers with different "tiers" each day, and each day we ran into something different. Perhaps our offers were a little too complicated and we could have built things differently or simplified them but in the end we just felt that the cart did not deliver with our expectations. The other item we requested as an enhancement was to allow scheduling and un-scheduling of the various smart carts we had prepped i advanced as I had to get up at 4am my time each night to change the offers. 🙂