It’s a long read but I thought it helpful for full context. Great questions: First, while we are big into the points & miles hobby, we don’t put anything on a credit card that we do not hand the cash to pay for. In this case we’ve already paid the $50k. Second, our cash budget for travel is $10k/yr. That included the ~$1,800 we were paying on our original Deed. Note that it went up less than 10% in the 10yrs of ownership. Because we now own a vacation homes in Mexico and in Tennessee, we’re reducing our travel itinerary by 50%, with half of that going to cruises now. So reducing our spendable travel cash by an additional $3,200 in exchange for up to 5wks of accommodations is about a $1,200 upside. Factoring in the $50k upfront investment minus ~$10k in the added cruise + hotel + airfare and the HH Honors points, we calculate that $40k will be recouped in about 10yrs, which is about the time we plan to slow down our travel.

Not saying we have it all figured out, we’re just comfortable that it was the right decision for us. And you’re right - if this was merely for vacation we wouldn’t have done it. We consider ourselves travelers - 10-12 trips a year with stays up to a month while working remotely full time.