@uaremymuse 60% of the time it is a bad use of money if you buy resale and 99% of the time when you buy from developer. Like anything you have to pick what's works and if it doesn't work for you then it's not a fit. Simple. Renting is risky and there are a lot of low quality AirBnBs out there. But we also use renting when it works. It doesn't have to be all or nothing. you are a financial guy, so think portfolio e.g. very selective timeshare, some rent. It's like stock picking...
Here is how it works for us. We travel during peak season in Maui and Oahu and want oceanfront at top resorts. We purchased an EOY Westin OF for $12k resale. These units rent for $5000+ per week during the summer. Three rentals and we have spent $15k+resort fees with nothing to show for it. With owning, we have ROI vs. renting after 3 visits. Even better, we can lockoff the unit and rent half for the cost of MF = Free stay (or small profit) for one week in OF at the Westin, or we can lockoff and get two weeks out of the MF = $1400/week in OF in HI during peak. You can't rent similar unit for anywhere near that price. If the lockoff rents for $3,800 then we are ahead $2,400 per WEEK or saving $4,800 vs. renting those two weeks.
Last summer we had a 3 bedroom penthouse at the Lagoon Tower at Hilton Hawaiian Village over the July 4 holiday. Our cost was about $1000/week. The room rents for $2500/DAY. We recouped the cost of a TS we purchased with that single trade by 4x vs renting (if we could even find one to rent). Our timeshare that we traded still has resale value but could give it away easily tomorrow and still be way ahead financially.