If there is a serious possibility of an either/or opportunity then surely you are better not touching in until you know which way you are going. Otherwise you run the risk of missing the bus while you get out of the station?
Admittedly this only happens in some places where there's a good view from the station, but I have been caught out on Sundays with 1tph.
At most stations you will start a new journey straight away if you touch in straight after touching out. Which station have you found that you have to wait at?
I can't think of any examples other than South Ruislip but I left the station for about 5 minutes, tried to touch in and had to wait a few more minutes before it worked.
Then you'll get a third off all off-peak rail tickets (inc tube/dlr)... You even get the discount off the 1-2 and 1-4 price caps which you don't with a paper travelcard.
I have done and had forgotten about the single journeys, although even a return local trip of one stop by train and a bus journey will just about reach the 1-6 cap. The discounted 2-6 was very good value until it stopped recently. The 1-4 cap doesn't apply as I live in zone 5.
Whilst there is a known problem with some post midnight travel I'd be interested to know where you've hit issues.
This is mainly travelling by bus, Oyster ends the day at midnight and a paper Travelcard at 04:30.
Edit: Will future Oyster cards have both ITSO and the current system on them? I don't see the cards taking a few seconds to read working very well in any major city.