The DTV visa's primary concern is your intended date of entry into Thailand. Therefore, you should go ahead and secure your accommodation and flight bookings, and then use that information to submit your DTV application.
Since your planned travel date is in January, I strongly advise you to submit your application before December 20th, as the consulate will observe a 5-day holiday period for New Year's.
I did the entire thing alone and got approved. It takes time and is a little complicated, but attention and focus will certainly help. I think you'll manage, hit me up if you need assistance.