It's not the time you land, it's the time you pass immigration. I had the opposite situation....was second in line at 11:55, so let the person behind me go ahead. Got stamped at 12:01.
that was my point, POOT is an airline policy, not Thai immigration, and that's what the embassy told me. So best thing is to confirm with the airline you are flying as to what they require for you to board flight
I visit my gf about 4.5 to 6 months total each year (2 trips) and I've concluded there's really no advantage getting anything other than TR/visa exemptions and extensions.
the requirement is to have an onward ticket but doesn't need to be within the initial visa term. I have this in writing from the embassy and they also warned me that airlines policies could be different.
The requirement to have POOT within visa duration is actually not a Thai requirement however airlines have their own interpretation (as explained to me by Ottawa embassy). Therefore it would be best to simply confirm by email with airline you are booked on what they require.
Re #1. Not a problem - ppl saying its not allowed are being overly pedantic. Similarly a CEO on vacation making a call back to the office is "working" and technically this is not allowed, but no one is going to care. As long as you are not providing services to people in Thailand you are fine.
Same thing happened to me (Ottawa embassy). 3 weeks heard nothing, then get a message to send more docs. This was 4 days before my flight. I sent what they needed right away and they told me it would take another few weeks to process. So ended up going visa exempt and had a 1 day overstay, which was waived. I eventually received the visa and luckily can you it for my next trip in January. So in the end I actually saved money LOL