I'd say no, wait at least until you need to change the chain.
You might even be able to run a 3rd chain before flipping the sprocket and chainring.
On hub gear bikes with "normal" sized sprockets I generally run 2 chains on one sprocket without flipping, swapping the chain every 500 to 800 kms to ensure even wear. (I then clean the chain so it is ready to be swapped back on next time). I do this until the chains are significantly worn.
If it is possible to flip the sprocket (not always, with dished sprockets the chainline can be significantly out) I then run 2 other chains with the sprocket flipped. By this time the chainring is generally fairly worn, if it is possible I then flip this and start again with new sprocket/chains.
This is for family bikes without a Chainglider.
With my bikes that have a Chainglider, so far I haven't done much beyond taking the Chainglider off now and again to take a look, then putting it back on again. But I haven't yet done a huge mileage with Chaingliders.