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Available ships, scheduling, and student to instructor ratios:
You should be able to train as often as you want given reasonable notice. Small, individualized programs may offer a distinctive, thorough, and personal training experience, but there is the risk of a delay in training if the staff or fleet is particularly small and therefore vulnerable to circumstance. On the other hand, larger schools offer stronger fleets and the solidarity that comes with training usually standardized by Part 141 regulations, but the training process may be impersonal.
Is R44 and turbine transitioning important in training?
I don't think so. It certainly can't hurt if you have the money to spend, but lack of transitioning won't put you at a significant disadvantage when beginning your career. I've also heard that transitions will likely be available to you later at no cost depending on your job.
Why are full-down autorotations important and why do some schools charge a higher rate for practicing them?
Full-down autorotations are important because your safety as a helicopter pilot is in no small manner directly related to your ability to glide the ship to a safe landing should the engine fail. Some schools do not practice full-down autorotations for insurance purposes. While I'm sure you can train well at these schools, I'm of the opinion that touching down completely is a much better practice exercise for a maneuver so critical, even if the increased risk involved means higher training costs.
What's TRACON?
Terminal Radar Approach Control, which handles the intermediate airspace outside of the airport's ATC before (or after) an aircraft is controlled by the regional Air Route Traffic Control Center (ARTCC). It's nice to train at a school that takes control from a tower; it gives you more experience.
More information on: How Air Traffic Control Works
IFR Simulators:
They reduce training costs. Though realistic, they're obviously not the real thing.
Insurance: Watch your back.
Accidents happen, and deductibles may be 10% of the value of the aircraft. That's a substantial ding in your valuable training fund should you have even a minor incident in a $220,000 R22. Many schools assign no liability to the student or allow you to exempt yourself from the deductable for a small annual fee (a few hundred dollars). I would suggest opting for these schools. But keep your guard up if you intend to instruct as a CFI - these same schools often instead assign liability to the instructor who is PIC at the time of the incident!
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