after making the dagger, the improve them as that only uses 1 bar and gives skill, compared to making 2 daggers you save yourself a ton of leather if your making a large batch.
But at the fastest, you'll still be running all over Whiterun to get this done. Plus, improving an item barely moves the bar at all, whereas simply creating a new item vastly moves the bar forward.
On the topic of Iron Daggers vs. Leather Bracers, I always choose the Leather Bracers. It is much, much cheaper to go with Leather as you can make the other ingredient (Leather Strips) from the Leather itself. If you go with Iron Daggers, you still need to buy Iron Ingots which are vastly more expensive to get the same amount you need to create enough Daggers to make it worth your while.
Leather Bracers are easier, cheaper, and over-all better to produce than Iron Daggers. I wouldn't even woryy about enchanting them unless two prerequisites are filled. 1) You have a mono[oly on the Petty Soul Gem market. 2) You
really need to raise your Enchanting Skill. While the money is nice, you are still going to be taking a tour of all of Skyrims forges if you are wanting to get your Smithing Skill to 100 in as little time as possible. Otherwise you will be waiting for an eternity for the Blacksmiths to restock Leather and Leather Strips.