Welcome to the forum and welcome back to the A&A hobby. It sounds from your current situation that you’re well-positioned to spend many enjoyable hours with the game – perhaps even much more time than the folks here who aren’t yet retired (though I must say that the various friends I know who are retired sometimes give me the impression that they’re even busier than people who are still working).
Anyway, here are a few thoughts about the points about which you’ve asked.
A&A 1941 is a good choice to reintroduce yourself to the game (and to introduce your family) because it’s the smallest-scale and simplest of the A&A board games that are currently being produced. It’s also the cheapest, so I’d recommend buying two (or more) copies, for three reasons. First: that will give you a more adequate number of sculpts than just one copy. Second because the non-infantry sculpts in the game are different from the “mainstream” sculpts found in the other A&A games – and as such, they may become hard to find if A&A 1941 ever goes out of print. To this day, I still regret not having snapped up multiple copies of A&A Battle of the Bulge when it came out rather than just one because it contains cool truck units that have never appeared elsewhere. I haven’t made that mistake with 1941; I currently own…um, well let’s just say “several” and leave it at that.
The third reason ties into one of your other questions, which concerns the fact that the non-infantry sculpts in 1941 are shared designs, with all the Allied units of one type being one design and all the Axis units one type being another design. I’ll return to that point in a moment.
Moving upward from 1941, A&A 1942 2nd edition is the intermediate-level A&A global-level game. It uses mainstream sculpts (not the 1941 variant ones), and most – but not all – of them are nation-specific in design, and it has more unit types than the smaller game. The same is true for the final steps upward: Pacific 1940 2nd edition, Europe 1940 2nd edition (which is a bit larger in scope than P40/2 because it has more player powers), and finally Global 1940 2nd edition, which is what you get when you combine P40/2 with E40/2. G40 has the most player powers of any A&A game, the most unit types, and the biggest map. Some forum members have recommended that new (or new-ish) players ought to work their way up to G40/2 as a way to gradually acclimatize themselves, while others have recommended that they dive straight into it without wasting time on the lesser games; both viewpoints have some merit, so I won’t really get into that debate.
Now to get back to the 1941 game. As an A&A sculpt collector, the thing I like the most about the 1941 game is that it fills two gaps that exist in the A&A Global 1940 2nd edition sculpt array. In G40/2, all nine player powers have a distinctive infantry sculpt design, and most of the player powers have a distinctive sculpt design for each of the 13 non-infantry unit types. The three exceptions are China (which completely lacks equipment pieces), Britain (which lacks a distinctive naval transport design) and Russia (which lacks a distinctive aircraft carrier). Fortunately, the Allied naval transport in 1941 is a British design, the Allied aircraft carrier in 1941 is a Russian design, and the Allied fighter plane in 1941 is a P-40 Warhawk which fits the bill perfectly as the single Flying Tiger aircraft that China is allowed in the 1940 game. The 1941 game can therefore be used to fill the distinctive-sculpt gaps in 1940, which is an added reason to buy multiple copies. (Arguably, this still leaves China without a distinctive sculpt for the only other unit it’s allowed to have, which is artillery. My solution to that one is to use the pale green artillery pieces from A&A WWI: 1914, a game which – like the original Milton Bradley edition – uses generic non-infantry equipment pieces for all the player nations.)
You can find out more about the A&A sculpts by consulting the unit identification charts which I posted here…
http://www.axisandallies.org/forums/index.php?topic=31982.0
…and the table of G40/2 units given on the back pages of the E40/2 and P40/2 rulebooks, which are available for download here:
http://avalonhill.wizards.com/rules