Thanks to all for the informative advice. It sounds like obtaining the non-immigrant visa in your home country is a good first step followed by some good ol' research in Thailand with some retired expats who have gone through the process of obtaining the retirement visa.

With that said, I've found the following information to be a good start:

STEP 1: OBTAINING A NON-IMMIGRANT " O" VISA
If you want to retire in Thailand, you need a non-immigrant visa. Ideally, it should be acquired prior to your arrival in Thailand.

Requirements for getting a non-immigrant visa outside Thailand:
1. 50 years old of age or older
2. Passport (at least 1 year remaining until expiration)
3. Holding the nationality or permanent residence of country of application
4. Police Records Check
5. Certificate of Health
6. Proof of meeting financial requirement *
7. Bank letter showing funds or pension statement


STEP 2: OBTAINING ONE-YEAR RETIREMENT VISA IN THAILAND
REQUIRED DOCUMENTS:
1. Passport - copies of every page. Each copy must be signed by applicant.
2. Non-Immigrant Visa
3. Departure Card TM.6
4. Proof of meeting financial requirement *
5. Thailand Bank book (original)
6. Letter from your Thai Bank
7. Medical Certificate (health exam administered by doctor at first class hospital)
8. Photos, three (3) in quantity which are 4 x 5 centimeters in size (not passport photos) with full face and taken wearing business attire (no hat and some jurisdictions require suit and tie). Must have been taken within six (6) months.


* FINANCIAL REQUIREMENT:
1. BANK ACCOUNT SHOWING THB 800,000
2. MONTHLY INCOME OF AT LEAST THB 65,000
3. COMBINATION (BANK ACCOUNT + INCOME x 12 = THB 800,000)

Signing for your new Retirement Visa
Your first and only appearance for the retirement visa will be at the Immigration office upon its approval. You must appear in person with your passport and sign the visa paperwork in the presence of the Immigration staff. The Immigrant staff puts a stamp in the passport at the time of approval.

Restrictions on Your Retirement Visa
The retirement once approved allows you to stay in Thailand for one year. You are not allowed to have employment while on this type of visa. Also you must report to Immigration every 90 days to verify your current address