It's not very silly at all, really--roleplaying is hard, man. :\ I don't particularly feel like I merit giving advice on this, but...I guess I could say, these are the things I take into consideration when writing?
-When starting a topic, always think in advance: who can reply to this? Come up with several characters that belong to other people, and imagine them being the ones to respond. Even if they don't, it's good sometimes to write like you're already expecting a certain reply. Don't make it too obvious who you're thinking of, of course, but try to avoid being so open-ended that you get dreaded comments like "I'd like to crash, but I can't think of any of my characters being in this situation."
-Again, for starting a topic: enter with something exciting. Introduce it however you want, but add in some sort of 'hooking' action towards the end that people can use when writing a response. (Obv, it doesn't have to be extreme, just some kind of action that merits a reaction.)
-Don't be afraid to take liberties, sometimes. I have a lot of trouble with this, but...I have to remind myself that people usually don't mind, and when used correctly, it can make the rping more interesting to reply to.
-If I haven't hammered it home yet, always write with the other person in mind. Constantly think of how can they respond. That's what you're really writing: material for the other person to work with. That's why it's okay to take liberties and whatnot, because you want to keep it engaging for both parties--the goal is (besides just writing to tell a story) to keep up a stream of replies. If you're not giving them enough material, then they might not feel able to write a reply, and the rp could slow down or stop altogether.
-Avoid using too much dialogue. I think I'm biased on this, because I tend to hardly write any dialogue at all (which isn't good, either). But if there's too much, then the other person may feel like they have too much to reply to. Which can also slow things down.
-Don't feel pressured to come up with long replies. This might just be me, but personally I don't feel like it's a big deal to get shorter replies from other people. It's better than it being too long, where I feel like "ugh, I can't respond to all of this". But idk, again, that might just be me.
-Don't ever feel personally hurt by what the other person writes--remember that it's all in-character. Idk if it's necessary to put this, but I know some people (myself included, formerly) have a hard time dealing with feeling offended right along with their character. That said, get into character. If you can, make yourself feel giddy, depressed, angry, w/e. Force yourself to really see from the character's point of view, and feel what they feel. Again, idk if it's necessary to say this, but it makes writing a hell of a lot easier.
-As for the characters themselves, the best advice I can give is to figure out their defining flaw(s), and exaggerate it. Not so much that it becomes flanderiztion, but enough that it keeps them interesting. If they're not so smart, make them borderline retarded. If they're insecure, make them full-out neurotic. If they're moralistic, make them a major Quran Bible-thumper. EXTREME IS GOOD. Focus on the flaws and/or quirks and accentuate them. Add in some virtues only as redeeming points. Remember, these are characters, not real people. If their personalities were entirely probable, things would get boring, pretty quickly. THAT SAID, don't ever, ever exaggerate an annoying personality trait unless the character is so well-rounded that their complexity makes up for it.
Hope that at least some of this is somewhat helpful--and don't worry, I think we all get concerned over how other people feel about our rping skills. ...I know I do, anyways. :I
