Change will absolutely happen. Our 1st visit to Maui was 2004 and I rented a OF suite in Wailea Marriott for $2100 and used Delta SkyMiles to book free airfare. SkyMiles are worthless now and that hotel doesn’t even exist any more but lodging rates skyrocketed over the next 20 yrs…, as did MFs. Started at $1700 and was maybe $3700 when I sold.
However, the pendulum did swing and rental/purchase prices for condos are down considerably from last time I looked 4 yrs ago.
Anyway, I considered buying because I hoped I could stay 1 month in the same unit with 1 phone call, which it turns out is not possible. But the economics of buying 4 weeks v renting is at WORST a wash given I'll be 60 next year and can only reasonably snowbird for 15-20 more yrs. Split the difference and call it 18 yrs for the calculation:
WKORV OF 2 bdrm are going for ~$35.000/wk to clear ROFR, so I’d have to take $140,000 out of investments now and lose ~18 yrs of compounded interest.
$140,000 @ 5% over 18 yrs is ~$343,000. Assuming I recoup my entire $140,000 purchase price in 2048, I lost $203,000.
As long as I can rent at WKORV for $203,000 ABOVE THE COST OF MFs over those 18 yrs, the worst I do is I break even. That’s $11,277/yr or $2800/wk. I doubt it’ll be difficult to find an owner willing to rent for MFs + $2800, even in 18 yrs, unless things REALLY change.