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Requirement You can Activate an Item with the invested trait only if it’s invested by you. If the item requires you to Interact with it, you must be wielding it (if it’s a held item) or touching it with a free hand (if it’s another type of item).
Please be ready to cite the specific over general to your GM when dual wielding or two handing and wanting to activate the Anklets of Alacrity, Boots of Speed, and Winged Boots.
Items you might want/need to activate in combat that also require a free hand with no escape hatch are the Belt of Regeneration, Bracers of Reflection, Cape of the Mountebank, Clandestine Cloak, Cloak of Elvenkind, Cloak of the Bat, Dancing Scarf, Demon Mask, Goggles of Night, Healer's Gloves, and Ring of the Ram. There are others, but they're kind of obvious you'd need a hand free without checking their action type or are likely to be done outside of combat.
Interesting. This actually makes activating most non-held items in combat very difficult. People don't tend to have a hand free. Either they're two handing, or wielding a sword and shield, or dual wielding.
The two-hander has the easiest time, able to remove their hand as a free action, activate the item as an action, and place their hand back on their weapon as a manipulate action.
Other people get really screwed though.
Technically, it's the same action economy for someone else to drop a weapon (free action), activate the item (action), and pick the weapon back up (action).
However, I tend to agree that you probably shouldn't need to touch your toes with a free hand to use your boots. :)
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I remember in 1e, there's a rule about specific rules having priority over generic rules. I think the reasonable approach is to assume that rule as well. Interact actions requiring a free hand is a generic rule; this particular item requires you interact by clicking your heels, which is a specific rule unique to the item, and therefore you can do so without a free hand.
Spot checking a few of those items listed, it looks like they are worn items. Which does mean having a hand free in order to activate them.
So 'clicking your heels together' is a bad description of the activation process. You could certainly click your heels together while wearing Boots of Speed and wielding a sword and shield - it just wouldn't activate the boots. To activate the boots, you have to rub the rune stitched on the side, or spin the tassel on the heel clockwise three times. Something like that. Something that would actually be an interact action.
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The description of those three items specifically say you click your heels to activate. Thus specific over general.
Yes.
But that is what I am proposing as the errata fix.
Change the activation description. Don't change the requirement to use a free hand and interact action.