I don't really understand why he chose to resign there. It really doesn't look or seem like he enjoys playing there and he chose to go back when it seemed pretty apparent Kyrie and Lebron were not going to change their playing style and they were signing a younger player at the same position as him for a ton of money with big ties to Lebron.
They could offer him the most money out of anyone and, technically speaking, a chance to win a championship.
I wonder how true that really even is. Obviously everything is different if they win the championship, but that didn't seem super likely heading into the offseason and it seemed like there were a number of teams that could have offered him a contending position. Also, isn't it possible he could get pretty equal monday with much better endorsement opportunities if he was playing in a system that featured his talents more than as a third banana in Cleveland. Plus, also, Cleveland. Maybe he loves cold weather.
That's why I said "technically" but I agree that Cleveland's championship odds are not high. Not just because the Spurs and Warriors are better teams, but because the Cavs have awful team unity.
To your second point, maybe, but Cleveland had his bird rights thanks to the extension he signed in Minnesota (KAHN!!!!!) so they could offer him more money than anyone else could have last summer. I think his train of thought was even if things continued to not go well, they'd trade him somewhere else because he still has value around the league. I firmly believe teams would still trade for Love if given the chance. It just might be as much as Cleveland would want.
Players like the money and they like a winning situation. If both are offered, it is hard to say no, IMO.