I've got more than a few thoughts, but for now, here's this:
1) Yes, 2 years is enough time to gain 44 lbs, IF YOU DO IT RIGHT. Years before, I would have said "no, it takes longer" but quite frankly, I've matured in my training views since then. Sadly, I learned the hard way since I didn't have anyone to tell me (and show me) different.
2) Yes you can do it naturally. Pay no attention to the peckerhead that said you needed a boatload of steroids to do it. It takes lots, LOTS of hard work and even more eating. But it can be done. 44 lbs breaks down to 22 lbs a year. Which is less than 1/2 a pound a week. You can gain a measly half pound in a week.
3) Your waist will not necessarily end up bigger than 32" when you are at your target goal of 200 lean pounds. However, you must, I repeat MUST accept the fact that you might have to deal with a 32" or more waist in the process of getting to that goal. I am not suggesting you reach the "overfat" level again. Not at all. In fact I suggest you stay away from that.
HOWEVER, countless aspiring bodybuilders and physique trainees' goals have been absolutely sabotaged by the guy's childish unwillingness to lose his 6 pack long enough to gain some fucking muscle. So, make the commitment for the long haul and get to it. Otherwise you will. never. reach. your. goal.
4) in the short term I'd tend to agree with you that low bodyfat % would look better on holiday. So work on that goal but when it's up, get into gaining mode. Set goals, short, medium, long term. They must be specific: if they are not specific enough, you can't track your progress and you'll get lost again.
5) 1 rep maxes have absolutely nothing to do with how you look. There is no number to shoot for that will determine how much like a cover model you look like. Maxes are great for tracking strength gains, and obviously more strength equals more muscle gaining potential, but in the final analysis 1 rep maxes are useless for "physique" goals as opposed to strength goals.
6) You can be 200 lbs and enjoy running and cycling quite easily. Hell you can rock climb effectively above that limit (although it is rarely seen). It's all in how you train.