Nothing wrong with being asked how long you will be staying for, particularly for visa-exempt folk.
US immigration asks this question (or similar ones) of most arrivals and it's the same in the case of EU/Schengen, UK, Australian and New Zealand immigration.
No, of course not. You'll either always be interviewed, based on your past history and have to put up with it or be even more likely to be interviewed should you spend as little time as possible outside of the country.
You'll have zero issues. In fact, immigration prefers people making regular trips out of the country and back on a DTV, rather than spending all their time in country and only exiting when required.
He's right about avoiding that border crossing for re-entering Thailand..I simply corrected him about his using the incorrect name for the border, that's all. Everything else he said was correct.
I just don't understand why farangs refer to a Cambodian town as the Thai border, when the immigration offices on both sides of that border work very differently. The Cambodian side, although surly, won't reject you, unless you have a history of overstays, are a political activist or from an "undesirable" nationality such as somewhere in Africa. Westerners will have zero problems entering or exiting Cambodia there BUT the problem lies on re-entering Thailand at Aran, on the Thai side.
Thus choose any other crossing, even nearby Ban Khao Din, which is very easy going.