TF2 contains 599 craftable hats and 5 special craftable hats, although most players will only realistically craft 2 or 3 of these. Older players would have had further potential to craft even more of their own hats, through bugs or those that are otherwise no longer attainable. For the purposes of obtaining a full collection of craft-hats crafted by you, you will likely be looking at the 599 in the craft pool, the SpaceChem Pin, and the Saxton Hale Mask. If you have not used your haunted scrap metal, you will also be able to craft one of the three Spine Skulls.

The question one must ask before attempting to create such a collection is what method minimizes my costs?
The SpaceChem Pin will cost you $2.49 - $4.99 on sale (based on isthereanydeal historical data).
The Saxton Hale mask currently costs ~227.19 ref or ~3.29 keys.
And the crux of this question and the reason you've probably found this page: the cost of crafting 599 random hats?

The following javascript simulations may help guide you to your answer. The simulation currently thinks random craft hats cost: ref.
Note that running large (>10) simulations may freeze your browser.






The conclusion to this page is that it is very foolish to not resell your duplicates (if they aren't already craft hat prices).
Crafting with only the rebuild headgear recipe is cheaper (>15%) than using tokens, however at a significantly higher (>20%) crafts required. The amount of resales between the two were rather similar so it really comes down to personal preference on if you want to spend more time or more money.

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