I'm now levelling the first toon I created (Kyresh MS/SR) after abandoning him for so long and even after a respec I'm still not happy with the build but I have to say I'm really enjoying the toon despite this.
I've got an unused respec I plan to use at level 28, which is just a bar or two away, so hopefully I can sort things then. I'm toying with the idea of only playing him to level 30 though and respeccing for PvP. I say that now though, but if I get the scent of level 50 I may change my mind 
I remember my first toon - an nrg/nrg blaster. Like you, I smile when I think back upon the power choices I made - how I was searching around for lvl 20 Training enhancements (Didn't know anything about DOS and SOs) and when I did, finding the shops where they were sold was another pain (Weren't clearly marked on the map as they are now)
Knowing what I know now, I'm sure he would be pretty cool - but in a moment of madness (possibly intermingled with embarrasment), I deleted him at level 20 (Not knowing about respec trials at the time..) 
I've learnt from that and now never delete a toon higher than level 10. My oldest toons (Booty and Peace) are now in their early 40s and have undergone numerous respecs as I learn more about each powerset and their abilities. 
Heh, I remember my first toon at release, an NRG blaster (can't remember the secondary though, probably NRG as well) and putting Range enhancements in every power, and wondering why I kept getting killed all the time
I remember the first time I made a hero...... Was an invul/axe tanker. Didn't even read any of the power descriptions just went..... Invulernability.....Coooool.......Battle Axe......Coooool
Even after that I messed up several power choices.... took manouevers, didn't take dull pain, didn't think fitness was important.
Praise be to respecs and all their saving grace.
He would never have managed to reach lvl 42 without them
i lvlled mine together at the start so made mistakes on 4 out of 5 toons which is still good really .
i stuck acrobatics on my scrapper at 20 who had practised brawler because i thought she sould flip around.
i had flurry on my blaster because haste never sounded appealing as i wanted an attack before ss.
My tanker Shannon was unbelieveably gimped at the start as i didnt know you could stack enhancements and ended up having 4 slots on the rest power cos i didnt know where else to put them (in those days base rates were higher tho ).
As my defender i didnt know why my heals were weaker than other peoples but my controller was surprisingly good, very good imo but in low levels slotting 1 slot of each enhancement does wonders anyway for a controller.
He will honor his words; he will definitely carry out his actions. What he promises he will fulfill. He does not care about his bodily self, putting his life and death aside to come forward for another's troubled besiegement. He does not boast about his ability, or shamelessly extol his own virtues. - Sima Qian.
The first toon i ever created (ahh it seems so long ago now) was a claws regen. Being new to the game lvl 1-15 took a looong time as i was solo most of the time. it was actually my girlfriend who pointed out that it was faster to team. I nearly made a few mistakes regarding choosing too many power pools instead of sticking with my primaries. As im sure most people will agree, when you are levelling you first ever toon all those powers look great. But having solo'd most of the way to 15 i found it better to obtain my primaries, mainly becasue they were the ones i figured that would improve my kill rate.
I Nearly picked the heal power pool, mainly becasue it seemed back then to be hard to find a good empath. (knowing what i know now i realise that an empath is a nice to have but not a must have) but agian i refrained. I went though the stage as im sure we all did of going to the hollows, doing the hover auto run put the kettle on, routine. but once i hit lvl 15 and got into team play seriously i started to get my head round the cookie cutter builds and tried to extrapolate on those. On reflection i could look back and say, it wasnt really necesary to get air superiority AND hover and i could also argue that maybe i didnt need to get recall friend. but i find they are all handy in their own way. (obviously hover is a bit of an accademic point as a scrapper unless im fighting sky skiffs, but i tend to just knock them to ground with air superiority and fight them on terra firma) the point im making through this rambling is that, unless you are really bothered by what other people think, make your first toon how you want to, in order to enjoy playing. I hardly ever use that toon now but i look back with a smile and think it was fun and i learned from it. and should i use him again. he can still hold his own and function as a useful team member.