Transition from Cash Basis to Accrual Basis

1) Yep, pretty much. But see below.
2) No, very often it is best to have just one account for "accrued liabilities" and have a huge reversing JE that itemizes what the items are (reflecting the accounts expensed) while avoiding having mirrored accounts.
In the CC example, you could do it your way (and in that case I would call the liability account "Accounts Payable"), or you could run through the JE process. In the CC example, however, it feels a whole lot more like an AP item than an accrued liability.

The most accurate method would require that you continue using the cash method until the very end of the fiscal year (e.g., period 12) and then start recording transactions using the accrual method in the first period of the new fiscal year. Otherwise, you don’t get true and accurate financial statements for the last year you were using the cash method. In your example, accruing the credit card statement expenses in period 12 would violate the cash method rule (although prepare you for the accrual method in the following period).

The easiest way to accomplish this is by doing what you are suggesting in #1 and then adjusting your financial statements to truly reflect the cash method throughout the current year. The adjustments should not be made in the accounting software for the current year. Then in the new fiscal year continue to record transactions using the accrual method. The idea is to make sure that revenue and expenses continue to be reflected in financial statements when payments are received and disbursed respectively. In the new fiscal year you can use a single accrued expenses liability account or several, probably by category (accrued payroll, accrued professional fees, etc.). Having a separate accrued expenses G/L account set up for each vendor would probably be unnecessary.

Another important step in converting to accrual is to adjust your budget for the new year to reflect the new accounting method chosen. If you have a planning and budgeting application that automatically generates financial statements, including a balance sheet and statement of cash flows, you will benefit from having the budgeted financial statement match the actual statement, which will make your analysis of actual vs. budget meaningful.

Okay, so if I'm understanding you correctly, I should not have any accrual entries or prepaid expense entries in any period of 2014. I should start with any accruals and prepaid expenses in January of 2015 going forward.

How would I properly reflect insurance premiums, for example that were prepaid in 2014 (either a month in advance or quarterly) that really pertain to 2015 periods? If I don't record the prepaid expense in 2014, am I not starting out 2015 with incorrect beginning balances?

Is there a checklist somewhere that would help in closing out the 2014 year and open up the 2015 year that I might be able to access? A step by step guideline of sorts....

My experience in past employment has always been one where the basis was already in place, not ever a situation where the company decided to change, especially after 30+ years of using the cash basis.