Yea, I think if you're somehow turning 1 million points into 6 months of stays, that will probably make the 30k work out. I don't know all the historic MFs vs rental rates, but assuming that things were similar or better before (many people on TUG say MFs used to be much lower than rental rates compared to today) and considering over 30 years - I could see it working out. Just assuming current MFs at CWA on a million points would put you at around $9k MFs. That's would be $1,500 a month. Usually we've been running numbers assuming around a thousand a week. Straight leases for 6 months probably aren't at $1,500 a month at anywhere with similar amenities as a lot of Wyndham locations. Forget about weekly (or is it every 2 weeks?) housekeeping. And those leases will usually charge utilities on top of that. So he was paying an average of $375 a week in MFs. This of course is in the age of "hard to beat rental rates" pricing, so let's assume things were more like 1/4 rental rates early on and slowly got worse (though I also dispute that this current rentals are cheaper than MFs is as common as the "Internet Wisdom" says it is, at least if we define it as open market, not RCI cash deals or good exchanges from another TS).
AI suggests a modest 1BR inland would run about 2x his current cost monthly, around $3,000 after utilities. Which means he's saving about $9k a year vs leasing and utilities... today. To do any sort of comparison I think I have to WAG it in todays dollars, so if we do a very rough adjustment with 30 years to 20 years ago starting at half again, so he'd be saving roughly equivalent today around $13,500 a year back then...
Asking some AI and it still seems like that retail purchase, even with getting such good rates - you can't make up a large up front investment. While AI calculates with taxes you'd have about $700k today, much less than the tax free calculation, my kinda week figuring above still only ends up with saving the equivalent of about $345,000. I suppose the turning point would be - lets say you saved $5,800 in 1993 vs renting that 6 months in 1993 dollars - would you spend that on something else or would this person invest that.
If you invested that savings, you get pretty darn close to the $30k lump sum. AI says $615,000 today. This is only considering federal taxes though, for both numbers. And it's only comparing against the most modest 1BR option, which I question if that is the right comparison. I think given how close this is - this is one case where I'd flip a coin.
Because we haven't valued the hassles with each method of snow birding 6 months - the bookings time with Wyndham vs the rental leases time in the other model. It's also pretty obvious that comparing to anything that isn't as cheap as 6 month leases gets blown out of the water, and we're assuming furnished apartments - I'm not going to even begin to work out managing your own furniture and appliance replacement schedules or half year storage etc.
After doing all that math, the only thing I am convinced of is that resale is just such a massive jump on the value vs retail and even "back when it was cheaper" gets lost in how well the stock market did over all the years.