"When some one brings up something sad or bad that has happened is "I'm sorry to hear that" or "Don't worry, it will get better" really enough of a response? Frankly I find it hard to offer these "words of comfort" when I find no comfort in them myself. As a realistic person, I realize that sentiment does not alter a situation so it's hard to be encouraging. Should I just say them regardless?"

One thing that could work in this situation is mirroring--something like "wow, I can't imagine how awful that must feel". In other words, communicate whatever the person is saying to you (through words, vocal tone, and body language) right back to them.

"When discussing something with some one there are occasions when I'm genuinely curious as to why they have a certain line of reasoning. I want to ask "why do you think that?" but it always comes off condescending. This is especially true when perhaps we are discussing a problem and I know the solution and they do not. I want to know what the reasoning behind their solution is rather than just telling them it's wrong or what the correct solution is--however when trying to ask them their reasoning I can't come up with a way to do it without sounding condescending. Should I not bother?"

How about "So what was your thinking here?" If that doesn't work, you could try being upfront: "OK, hm, I'm pretty sure that's wrong, but could you go ahead and explain your thinking to me anyway?" Then look thoughtful as the person explains their thinking, and then rub your chin as you say "OK, yeah, so I'm fairly sure that..." (Note the use of filler words and pauses at the beginning of sentences--I've found that if you hem and haw a lot when contradicting someone they seem to take it better.)

"When walking leaving my office and entering the hallway, how close should a person be entering the hallway from the opposite direction be before I wave or say hello. If I wait to long, they think I ignore them. If I do it to early, then theres a great length of time that we are both still walking down the hall and having used my throw-away "Hey" I have nothing left to offer them. It's awkward."

What works for me is to pretend that I don't see the person until we're close enough that there won't be much time to say anything beyond "hey". Another thing you could do is wave or salute when at a distance and leave the talking until you're closer.

"Is there a method/statement for suggesting an attempt at becoming friends with some one? "Hey, want to be friends" is unutterable for me. No matter how I imagine saying that line it feels pathetic. If I don't drink beer or coffee is there anything else to ask someone out to do in order to have some bonding time?"

Yeah, lunch :)

If you want to be friends with someone, there's probably a reason. Maybe you tend to agree on things, maybe the person has some skill or ability that you respect, etc. So just telling the person straight up what you like about them could be a good way to indicate that you want to be friends.

"How to accept a compliment. Thanks or agreement feels egotistical. Trying to act as humble by playing it down doesn't seem to be received well either."

When I imagine myself saying thanks comfortably, here's what I'm doing:

Saying "thank you" quickly while nodding downward and flexing my chin, thereby pushing my lower lip upward and outward in a sort of subtle, thoughtful smile. The pitch of my speech starts high and descends downwards rapidly. The emphasis is on the first syllable.

My theory is that the downward nod is the most important part--by lowering my head, I'm subtly lowering my projected status as I accept the compliment, making me seem un-egotistical.

Just using more syllables might also work well here: "Thank you, I appreciate that." The implication being that since you spent so many syllables expressing your thanks, the compliment the other person gave you was genuinely welcome for you to hear.