I have been looking at getting into pvp and have gotten some pointers and such from some veterans, but at the end of the day, the whole "don't fly what you can't afford to lose" attitude, while understandable, is very frustrating for me. To put it another way, I absolutely loathe frigates. I understand their value and purpose, but I prefer and have focused more time and effort in cruiser and battlecruiser piloting and such that relearning how to fly a frigate bothers me.
The other issue is, given the timing of when I'm on, I end up doing a whole lot of solo missioning and this gets boring. Yes, I can chat with people in various channels as I go about doing missions, but I've been stuck on l3 missions for two months now because I cannot afford to lose a Megathron or other BS. I've just finished putting together the fittings on the 'thron that was given as a gift; trying to insure it, will drop my wallet by 50% meaning that I wouldn't be able to even afford to fly my Brutix.
I understand that part of the game is to hurt the other person's wallet, but this in turn gives rise to many people who aren't willing to risk their shiny new ships. I've been playing MMOs now for just over 10 years, and the one thing that I've noticed, regardless of the setting/system/mechanics, I always seem to have a hard time making money in the games I play. I play to have fun, do the quests, and socialize. I typically will have enough money to get by and stuff, but even in the three months I've been playing EVE, I have never had enough money to both buy, fit, and afford to lose a battleship; this could suddenly change if and when I get around to doing l4.
As for the high sec/low sec...in the early days, I had thought that the missioning progression would eventually make players go down into low sec; and there are some missions in high sec that have a destination in low sec, but there is no actual 'natural' progression to move players from high to low in that regard. Also, given the one experience I've had (take mission, go low sec, finish mission, get ganked), right now, I'm less inclined now more than before of even going to low sec.
I know this might sound a little immersion breaking and not be in the spirit of EVE, but if CCP really wanted people to do more stuff in low sec, I would seriously recommend the following: take a feature from the pve/rp servers from WoW. Treat low sec as contested territory, but if a person isn't flagged for pvp (in this case, their safety is green) then they cannot be engaged and nor can they engage other players. Let players decide if they want to actually do pvp in low sec instead of using the whole 'CONCORD will stomp your ass if you do' protection of high sec. And one thing, as I look back at my pvp'ing in WoW...I flagged for pvp more readily in contested areas when I had the choice; if I came into an area that was being attacked by the Horde (yes, I was and forever will be an Alliance player) and I wasn't on a low level toon, I'd flag myself and help out the other Alliance players out. So, that would be my suggestion about how to transition people from high to low sec.
I guess it would also help if there were more unique or better rewards for doing things in low sec than high or null...from what I'm understanding, I can in theory stay in high sec and more or less get similar rewards from missions as I would from low sec...might be faster in low sec, but I don't risk getting jumped while salvaging after the fact. And from what it sounds like, null sec is almost safer to fly than low sec? Again, I would like to think that the ability to choose to do pvp in low sec might help move some players from high to low and potentially increase the pvp action there as people have the option and aren't stressing out all the time worrying that the gate they're heading to isn't being camped. Null sec, to me sounds like a place where if you go, you'd be flagged for pvp whether you like it or not, but then you can increase the rewards to make the risk worth the effort.