I've done it twice in the past - once with a Nissan Quest and again with a Corvette. If I had either pocketed the money or invested it in stocks, I would've been well ahead, even with the Corvette. Continuing to buy extended warranties is like winning once or twice in Las Vegas and expecting that in the end, you will end up with more money than when you started - the odds will beat you most of the time. It's statistics, plain and simple.
2001 Trans Am: A/C compressor failure at 112K miles, rear-end failure at 89K miles, wheel bearing and axle failure 2x at around 75 and 80K miles, water pump around 75K miles. All this work was done by friends and using non-OEM parts of sometimes dubious quality, re-using stuff, etc. so it saved me money as I was broke and in college, but I bet you can add that up at normal cost...
2002 G20: Transmission died at 110K miles. Repair by dealer estimate: $4400
2010 Jeep Grand Cherokee: Water pump ($800), transmission leaking (twice, no clue the cost, but it took a week for them to fix it the first time, I sold it the second time), and so...oh so much more...
2011 Z06: Delivered with a cracked fender, $2200, covered by dealer. Kept it 4500 miles/1 year. Amazing vehicle. Too "young" to form opinions of its life span projection.
2012 370Z: Sold at 34K miles, lots of issues with the brakes, and the transmission would grind on the first shift in cold or rainy weather. Dunno how that would go by 150K miles...
2015 CX5: Rear diff went out at 3Xk miles, $2800 repair (water intrusion was the cause, but warranty covered it), and after warranty: Leaking timing gear cover, leaking valve cover gasket, failed fuel-pressure regulator (total $1400 + the timing gear cover, which...?? Probably another several hundred, easy...).
In literally EVERY experience I have with a vehicle over 100K miles, much less 150K miles, this warranty will pay for itself several times over. Not only that, but it amortizes this cost at 3.24% (in my case) over 74 months rather than surprising me maybe when things are thin for all I know, or I just overspent on a vacation, or whatever. It also includes rental, towing, etc. services.
You do what you want, but I can point to every vehicle I have owned and after 60K miles and before 150K miles, point to plenty of money wasted keeping it habitable and on the road.
How many vehicles have you had with over 100K miles for comparison? That's not a challenge, it's a sincere question.