Hi Phil -
Sorry to hear about your health troubles. That is no fun at all.
I'm still very much in the accumulation phase of my collecting, so I'm not much of an expert when it comes to liquidating.
If I'm reading your post correctly, it sounds like you have a relatively short horizon in terms of liquidating your collection, potentially as short as just a few years. In your post, you raised the possibility of dumping some of your current pieces in favor of buying others, I guess with the hope that you'll make more money in the process because the newly acquired pieces will do better over the next few years, at least compared to the ones that you sell today.
My personal observation is that short-term holds are often challenging, at least when it comes to trying to make money for those of us poor slobs who aren't dealers. Selling some Jordans today to buy 50s and 60s HOFers to hold them for just a few years might work out for you. Or it might not. Over such a short window, I don't think any of us have a really strong grasp about where the market will go, and whether you'll come out ahead.
Naturally, if you're able to successfully play dealer by getting high retail on everything you sell, and on the other hand buying everything at 50% of retail, then go nuts. You'll probably be just fine, assuming you can actually buy and sell at those prices.
But absent that sort of really nice setup where you can buy cheap and sell for high retail, I would be inclined to not try to trade in and out of pieces just to make money. My inclination would be to keep doing what you're doing - selling off pieces as it makes sense. Although I might tweak your approach slightly in terms of ordering. My focus would be to sell off pieces that are at or near their all-time highs first, and then get to the weaker pieces later. Selling into strength is usually a much better recipe for getting top dollar, and in the meantime if you're really lucky, maybe your weaker pieces will strengthen by the time you get around to selling them.
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Trying to wrap up my master mays set, with just a few left:
1968 American Oil left side
1971 Bazooka numbered complete panel
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