I'd like to buy an Omega within the next couple of years, likely a Speedmaster. If I only plan to wear a watch once or twice per week (special occasions, nice dinners, etc), does it matter if its manual winding or self-winding (automatic)?
All depends on what is most important to you. Durability, accuracy, style, water and shock resistance? First question is usually quartz or mechanical?
I myself prefer quartz field watches for day to day wear. A nice automatic makes a good investment for dressier occasions.