Sorry to be snarky humorous rude ??? but it’s time to stop chasing status once you achieve Lifetime Status (LT).

In all seriousness, this is a longstanding debate and you’re exactly correct with “… the answer (that doesn't exist)…” and “… comes down to the individual, their financial situation, their family situation, their work situation...” I recall 10-12 years ago attending a presentation at a MegaDO about not chasing status. The discussion is completely different for a business traveler vs a leisure traveler.

Unfortunately achieving status has become more challenging over the past 20 years (in my mind making status more valuable, the opposite of a devaluation). Gone are the days of all miles (credit card, BankDirect) counting toward status on AA and gone are MRs (mileage runs) as an efficient means toward earning miles and status on all airlines. On the other hand there are now many more credit cards which include status benefits or include a head-start on status requirements. It’s prudent to limit the number of programs for which one chooses to chase status starting with 1 airline and 1 hotel program, more if additional travel (or easy opportunities) warrants.

Personally, writing as 95% personal leisure traveler I achieved my first status serendipitously about 20 years ago. After a western ski trip or 2 I had legitimately flown transcon (from NYC) or to Las Vegas (connecting in LAX or SFO) several times all on UA and in July received Premier status (25K miles). When I finished all my legitimate travel for the year in early December I had ~46,800 miles, saw that 25K status received 25% earned mileage bonus and 50K status received 100% bonus and decided to fly to FLL via ORD for lunch in the terminal before getting back on the same plane to fly to ORD and LGA to earn 3800 miles and Premier Executive (50K) status for the next 14 months. (I was so smug at the time and thought I was so smart, didn’t realize until finding FT 6-8 years later that what I had done, and did occasionally over the years, was a well-known and well-discussed procedure known as Mileage Run.)

Part of my pursuit of status, starting ~20 years ago, included shifting destinations for things I would be doing regardless. Instead of 3 or 4 or 5 annual ski trips driving to Vermont I flew to the Rockies or Vancouver/Whistler. Instead of driving to (required) CME (Continuing Medical Education) a few miles from home I found CME which required flying, usually transcon. Perhaps you might be able to shift some driving trips to flying trips, if business or educational related it could be tax deductible (a small additional perk). Hotel status for a nugget* is a no brainer: Hilton Diamond via AmEx Aspire card. Hilton has an extensive footprint, Diamond gets breakfast (in many Hilton hotels) and the AF of $450 is very easily offset via low hanging credits (airline fee $250, Hilton resort $250, annual free night) to result in at least $50 put back in your pocket every year.

If you have a reasonable path to LT status it’s probably prudent to pursue it as LT status does provide a good deal of peace of mind, even with ever changing benefits and procedures. Of course LT status is just like FF miles in general, it’s a marathon, not a sprint. Took me 35 years total flying including the last 15 years with occasional (1 or 2 annually) MRs to achieve LT status on UA.

(*Naval Aviation “nugget”: “A Nugget is a first-tour Naval Aviator or Flight Officer, especially applicable during their first deployment.” and/or “A nugget was defined as a brand-new naval aviator who’d just received his wings of gold and was now enrolled in advanced flight training.” - funny story in this link.)