Researching Fairline, Azimut, Princess or Sea Ray Yachts

Why not add Sunseeker to that mix? I'd put it far ahead of Azimut and Fairline and the 60-64' Sunseeker hull is a very good riding hull.
1. Yes for the most part
2. Yes
3.No, I wouldn't be afraid of a well maintained 10 year old boat.
4. It depends on the sea state and type of sea.

Here are another set of realistic numbers to look at. These are estimates off the top of my head. We bought a 9 year old 50 ft Viking Sport Cruiser/Princess flybridge with 700 hours on her. Very well maintained (in the first year we went from Long Island NY, throughout the Chesapeake, down to FL and the Bahamas and back to the Chesapeake with no mechanical problems.) In our 7 seasons with the boat we have put on 1200 hours (typical season is 200 hrs) and covered about 20,000 miles. I do most of my own work (I have many years of mechanical experience with racing cars and boats) but pay to have major engine repairs etc. Engines are CAT 3208 TAs and Twin Disc gears.

In those 7 years of routine longer distance traveling we had to replace both aftercoolers as one had just started to leak, rebuild fuel injection pumps due to small leak, have the aftercoolers off again for clean and inspect, we had a major engine problem and replaced with a CAT Reman with full rebuilds on turbo, etc., had to replace a shaft due to a small crack at the keyway and did both cutlass bearings/dripless shaft seals/props all together, replaced engine/gear vulcan drive couple and had gear gone through while it was out, no problems with trans but vulcan couple failure was related to the engine failure. (less than 60K total over 7 years for major mechanical work).

I have replaced one Chart Plotter, replaced the auto pilot pump, new ram, new control computer and one steering pump (cause I could not get the old steering wheel off), trimtabs motor, both vacuflush toilets and vacuum pumps rebuilt, a few gauges rebuilt, new refrigerator, rebuilt ice maker, new flat screen TV, random electronics, a few plumbing repairs (Princess used Hans Grohe so pretty reliable). I replaced all of the canvas professionally (3.5K) but did the snap installation myself to keep costs down - cut the costs by more than half.

I do all of my own routine annual maintenance on engines, dinghy, generator etc. so this is maybe 1K per year. Bottom paint every two years (1.5K per occurrence). Every year, either a few batteries, water pump, macerator pump etc. Wax boat a few times per year – I do some myself and pay sometimes. Every year some interior/exterior latches or hardware needs repair/replace (just replaced all interior door handles and cabinet buttons). About to have from windshields resealed and next year will replace exterior soft goods.

It makes a huge difference whether you are mechanically inclined and do some work yourself or have to pay $100 an hour to get work done which is done correctly maybe 50% of the time. In addition to the above, annual dockage (varies whether we happen to be staying on the Chesapeake or in FL) and fuel (2.5-3K gals per year typical) and dockage while transient (6-8 weeks per year), are the main expenses. A 55 to 60 ft boat will cost more with 1 more head, bigger engines, bigger shafts/props etc. but hopefully these typical repairs above for a 10 to 15 year old boat can help you estimate realistic costs.

The engine failure was due to a crankshaft failure the cause of which was not immediately apparent. The engine had never been overheated, fresh oil annually, all service schedules strictly followed, etc. We cruised long distances at a reasonable 2100 to 2200 RPMs, engines met rated WOT, engines use about one quart of oil per 100 hours with no noticeable smoke at cruise. No evidence of injector failure, piston or ring failure etc.

Our best guess is that a few years prior I was waiting at a bridge on the ICW and moved over for a police boat only to hit something at idle speed hard enough to stall the engine, and damage the prop, slight shaft bend and tear up the drive saver. So maybe that put some micro-fractures in the crank that later led to failure.

The owner next to me in a Azimut 55-60 feet said he budgets less than $25 K per year on maintenance/unexpected repairs; his boat looks to be about 10 years old.

Does he do all or most of the labor himself?

IDK, but he does have a service wash the boat weekly.

I think he could maintain the boat for that amount, not including any major items being replaced such as major engine/generator repairs, canvas/cushions, etc. Perhaps he includes them as capital expenditures or improvements and not maintanence items.

Some of those numbers look really high to me, folks. We live aboard our 55 Grand Harbour (fly bridge) in the USA, and in the past 2 1/2 yrs, including doing America's Great Loop and doing 98% of all maintenance, we wouldn't have spent anywhere near what you are talking. Our girl is a 1999, and we have normal maintenance issues with her, and spend less on dockage than is quoted here. We make sure we either anchor out 2/3 of the time or marina at no more than $2 p.ft. We spent $11k on fuel last year, motoring most of the time (get 1.1 mpg) and due to weather spent 51% of our time in Marinas, vs at anchor. Always anticipate spending more than less! You don't paint your boat each year, but you do have a diver clean her bottom, every six weeks or so when in a Marina, and you have other costs associated with staying put. If you don't want to do most of the maintenance yourself, or cant, then those figures might just be closer than we think!

I think for 60 feet in the Med I would budget around 50k EUROS a year.

This including a yearly marina fee, lift-out with anti-fouling, and engine service. Those about 25/30k alone.
I would add double to that for other extras as cruise and usual extra maintenance expenses.