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Hiow How to handle multiple inflight transactions from same address?

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Hiow to handle multiple inflight transactions from same address

How are multiple inflight transactions from the same address handled? From my understanding, there are two options depending on how change is handled, but both seem to have substantial drawbacks:

  1. If change for each transaction generates a new address for the change - the usual handling - then you can't handle two transactions since they will both want to use the same unspent output address. And they will both use it entirely by definition. The ergonomics of this seems poor - I can only ever do one transaction from an address at a time. In that case I would want bitcoins sent to me to always be shredded (no bills larger than $20 please).

  2. If I have change sent sent back to the original address, does it matter in what order they are added to the chain? I can't see why. This however allows everybody to track my wallet and where I'm transacting. Also I don't know if all wallets support this.

Is my understanding correct? (This all started with me diving down the rabbit hole on how Lightening and Plasma worked.)