I like to repeat with the SPs that really gave me a wonderous session. The ones that combine beauty and service to the best degree. As said by OP, there is the part of craving for the session on more than just pics or expectations, you know more or less what is coming.
But there is always the craving of "new adventures" as well that sometimes make you want to experience new things. Either you saw the lady in a party, or the pics talk to you a lot, or the description etc etc.
What i try to do is go for 2 new ladies and then a repeat when possible, or sometimes if i had a disapointing meeting, i go see someone i know ill have a great time, that never disapointed. I only go see providers 6-7 times a year nowadays, so im always hoping and trying for the best possible meetings .. So this mean highly reviewed SPs and such most of the time.
In any case would i be more at ease financially, i would have regulars for sure. There is just a chemistry that happen when you see the same provider, she know what you like, how to please you.