For this, or any cap chain, it all depends on the number. If you have only 2 Ospreys, they can use both on each other. But usually for more than 2, you create a squad or channel for logi, and put one of your cap transfers to the person above you and one to the person below you, either going by fleet order, channel order, etc. If you hear someone say logi cap chain that is what they are referring to, and you may hear the short phrase "go one up one down" in reference to how they want the chain, and the Logi commnader/anchor announce "chain is up" after a warp or jump so that the FC knows the chain is established and reps are inbound.
In this case you need to keep at least one Xfer on and from another logi, but can do a couple of cycles to a different ship without losing all of your cap, then xfer it back to the chain partner to bring you back up to full cap stability.
In the case of T2 Logi cruisers, particularly if you have Logi Cruisers 5, you get such bonuses to cap xfer and have enough fitting room that some fits can be stable with only one cap xfer, freeing up another slot for another remote rep, although in some fleet comps some of your logi will still keep this spare cap xfer for combat cap xfer, or if they only have logi 4, then they may need it to feed their cap partners.
The tough part, in that case, is if you mix a logi squad with people with logi 4 and those with logi 5, you have to decide deliberately how to arrange them and their cap xfers, either by using different fits for them, or by requiring the squad to maintain a different cap chain patter than the "one up one down"
I'll see if i can dig up a post, if not I'll write one on cap chain and logi in general.
Rambled on answering more questions than what you asked, but i think i answered you too lol