Would It Be Crazy To Turn My Stay-cation Into A Plane-cation?

My wife has a business trip next month that will end with her in New York City on a Friday, so I’m planning to join her to spend the weekend there. She’ll actually be traveling for a whole week leading up to the weekend, so that gives me several days at home by myself with no adult supervision.

It’s been a rather crazy first few months of the year at work so I was actually thinking of taking a couple days off that week for a stay-cation and some much needed “me time”. At the same time, I have a ton of miles burning a hole in my pocket, and am getting the travel itch since we don’t have any international trips planned until October.

Then the idea dawned on me, why not do something that satisfies both desires? In other words, why don’t I do a stay-cation where I’m traveling, but at the same time not really traveling. So technically, this would no longer be a stay-cation, which is defined as:

stay·ca·tion

ˌstāˈkāSHn/

noun

informal

a vacation spent in one’s home country rather than abroad, or one spent at home and involving day trips to local attractions.

1. Sit around the house all day in my pajamas
2. Catch up on all the TV shows and movies that I’ve missed
3. Surf the internet and watch Youtube videos for hours on end
4. Eat and drink whatever I want since I’m technically on vacation
5. Sleep 8-12 hours a day including countless naps

• Singapore First Class: depart SFO at 0115 on Wednesday, land at HKG at 0635 on Thursday
  • Cost: 70,125 Singapore Krisflyer miles (transferred from Citi ThankYou points + $23.40 in taxes/fees
• Hyatt Regency Tsim Tsa Tsui: 0800 to 2100
  • Cost: $0 by using Chase Hyatt Anniversary night
• Cathay Pacific The Pier First Class Lounge: 2200 to 2400
• Cathay Pacific First Class: depart HKG at 0030, land in JFK at 0700 on Friday
  • Cost: 67,500 AA miles (+10% rebate from Citi AA Platinum card) + $50 taxes/fees

• I will have roughly 36 hours, or a day and a half, of flight and lounge time where I’ll basically be doing exactly the 5 things above that I wanted to do. Except that I’ll actually have better food and drink at my fingertips than I’d normally have at home, like lobster and champagne instead of pizza and beer.

• The only reason I’d consider this option is that all the flights are ultra long-hauls of 14+ hours (HKG-JFK is a through flight that stops in YVR for an hour). Based on my experience on these types of flights, I should be able to get 6-8 hours of uninterrupted sleep each way
• With more miles to burn than time to spend them, in my mind the opportunity cost of spending these miles is low. So I’m actually saving money on my flight from San Francisco to New York by doing this, despite the taking the scenic route to get there. Also, this is essentially my last chance to fly Cathay Pacific First Class before the upcoming AA devaluation later this month, after which this redemption goes from 67,500 miles to 110,000 miles

• If I was at home I’d actually be more likely to check in on work emails; at least the time on the plane will truly allow me to unplug and get off the grid
• Lastly, I don’t really view Hong Kong as a destination where I’ll feel obligated to be out and about to see and do things since I’ve lived there in the past. In other words, I’m happy to have a nice meal, do some quick shopping, and then spend the remainder of my 18-hour layover relaxing in the hotel or at the lounge