Best Japan job start date?

So, I am a US citizen and work for an American company and am transferring to our Japan branch.

They gathered my passport/info in the past 2 weeks and I got the offer yesterday. I will be paid in Japanese yen. Also my healthcare will change to their plan in Japan.
However, they say the start date depends on the visa.

I was thinking 1/1/2014 would be best for these reasons:
-My 2014 taxes will be simpler
-My healthcare situation will be simpler (the coverage goes from 1/1-12/31/2014)
-My salary payout will be simpler with the company

[Q1] How true are these reasons? Do I need to hire an accountant in Japan and the US??

[Q2] Can I enter Japan on 12/26/2013 even if I started work on 1/1/2014?

[Q3] Does my below plan look okay?
-Decide on a 1-month furnished hotel/hostel/guest house before leaving the US
-When I arrive in Japan on 12/26, stay in this hotel
-Open a Japanese bank account
-Search for a more permanent apartment
-Settle in to the new culture (only been there for 2-week vacation once!)

How do you figure healthcare situation is simpler? You get on national health insurance and start paying.

Also, how do you figure salary payout will be simpler? You work. You get paid.

You won't need an accountant. The IRS 2555 or 2555-EZ form is pretty straightforward. Unless you make over roughly $93,000 here, you won't have to pay any U.S. taxes.

Enter any time you like. The problem lies in how long the job is. A year, presumably. So, if you come in December and start on New Year's Day (officially, that is, because the company will likely not be open that day), your visa will be good for...how long? You might get one good for only a year, in which case you'd have to renew for the last few days in your contract (not a biggie, but the J branch might find this uncomfortable). If you get a 3-year visa (no way to know, and no real way to guarantee it), you are covered easily enough for that year.

To open a J bank account, you'll likely need an inkan and MAYBE some paperwork from your employer. Confirm. Plus, your employer may prefer a certain bank.

Why are YOU searching for apartments? Doesn't your employer take any responsibility in that? You're the one traveling thousands of miles to work for THEM!

Glenski, thank you for the reply and sorry for the late response.

I asked to be transferred, so the employer is not helping me find apartments (but they are giving me some money to help relocate).

1. My job is indefinite (retirement age is set to 60?).
2. I guess you are right that the medical insurance and taxes are not too much of a hassle. The start date is not really in my control either. It depends on visa processing time, my current manager, and my new manager.
3. I will check regarding the bank with my employer after things settle down a bit.