May sound very plain of me to say, but I don't have much worry
Transaction safety: We're doing it through a trusted place, or nowhere at all - Its that simple
The cycle of selling is probably the part that is different from person to person. If you own thousands of domains, its a different ballgame compared to someone who has under 50. Less headache if you own a small amount of high quality, than thousands of "lesser quality" ...myself, I own a handful of "reasonable quality"
Regarding money ...your price will either be met, or you're going to compromise ...that depends on your level of satisfaction
Things don't need unnecessary worry ...roll with it