@OP: I posted before, as you requested, to talk you OUT of a BP/W. But:
If you know you're going to start diving doubles within 18 months, then you're going to need to buy a BP/W setup. In which case, you may as well start with one and just buy a doubles wing later.
I have a SS BP (2, actually) and a Kydex. I almost never use the Kydex.
Flying with a SS BP has not been a problem for me. I have flown with mine to Mexico, Hawaii (twice), and Las Vegas (Lake Mead). I fit my BP/W (with SS BP) in my rollaboard carry-on bag. Along with it, I fit my mask, wetsuit, and a few other items. I carry my regulators in my "personal" item. So, the only scuba gear I put in my checked bag are my fins (and miscellaneous accessories and tools). With the SS BP and other stuff in my carry-on bag, it has never been subjected to a weight limitation. But, the carry-on DOES weigh less than 50#, so I can't foresee it being a problem, even if someone did want to weigh my carry-on bag. Airport security often does ask me "scuba gear?" when they x-ray my bag. Usually, they don't even bother to open it up.
In other words, in your situation, I would just buy a SS BP and be done with that aspect of the decision-making process. I would also go with a 30'ish pound wing. to cover your cold water diving and also use in warm water. You might eventually decide you want to get a smaller wing for warm water, but then again, a lot of people have no complaints about using a 30# wing in warm water. I would not have bought my 23# wing except that my 30# wing is a horseshoe and I wanted a donut, and the 30# is older and has proven to be a bit fragile.
With a SS BP, the only time I would think you might be especially over weighted is if you dive in board shorts and you use a steel tank. Most warm water (for you, based on what you've posted) is going to be a flight destination and you'll be using rented tanks. Which most likely means aluminum. And with an aluminum tank and a SS BP, even if you are diving in board shorts and even if you are over weighted, you won't be so overweighted as to be a problem. I mean, an SS BP is only 4 - 5 # heavier than an AL one, right? And you probably won't be overweighted anyway (with an AL tank). When I use my SS BP with an AL tank and my 3/2mm suit, I normally add 8#, in salt water. I might be 2 # heavier than I need to be, but it's close. With board shorts and no wetsuit, I think the SS BP and an AL tank would be very close to perfect (for me, anyway) in salt water.