I wish I could provide concrete answers, or opinions to your questions...There are so many variables, especially the build and swagger of the man wearing the heels...
Anyway, I would agree that bare feet or hose/tights are best for heels, no socks..
Some guys, especially tall men, with long legs and a swimmer's build, can pull off most looks effortlessly....Then, there is the rest of us guys, who don't quite fit into that category. So, all I can say here is that what might work fine for one man, can not look so good on another...Wish I could be more concrete, but there are hundreds of variables that affect the look...
To me, most guys look better in jeans with heels, but that is just my opinion...In any event, the jeans must fit correctly, and be the proper length, or they can really detract for his appearance in heels..Like FF has said, very loose jeans that are too short are usually a no no...
Seasons, hmmm. Oh well, I'm sure there are seasonable looks, I just wear my boots and jeans the same way all year...
As for "no nos", again the variables are so many that it is hard to even generalize...Again, usually only slender tall guys can pull off extremely feminine looks successfully. So, the rest of us kind of need to be able to blend our heels with more masculine attire.