I agree strongly with the incremental approach. It prepares you for the inevitable glitch, (your server goes down or whatever). You have lots of options, and can move as slow or as fast as you like. The more you do the faster you will get and the more you use templates, the better they will get.
I entered my complete ROS and PE as single paragraphs, (13.Cardio-mts Cardiovascular: Denies palpitations, tachycardia, heart murmur, irregular rhythms, chest pain, exertional dyspnea, cough cyanosis, ascites, edema, intermittant claudication, cold extremities, phlebitis, varicosities, postural or permanent skin color changes. Also denies hypertension, rheumatic fever, or taking medications for heart disease.)
But note that I began each system with a number. That forces Amazing Charts to list them in the correct order, instead of alphabetical order. And the number is a decimal because I have gone back and added additional pieces as needed. Finally it has my initials because we are three in this office and we share the templates, and delete what we don't like, keeping my initials on mine helps me to find my own.
Also I want to point out that you should prepare with the complete H&P but that is about all. Over 80% of the templates we have were created in real time with the patient in the room. And MOST of the other templates we tried to make in advance, just don't get used.
Finally I would suggest a template for the HPI that states: " This entry does not represent a patient encounter, but is a note saved for the purpose of entering data from the old paper chart". You have to save anything you put in the PMedHx or Soc or Fam by saving the "Note" and it saves time twice if you use a template. Make the note quicker and recognize it for what it is when you are looking in old notes.