Is it always best to just have the client create a new contract with updated terms just to be safe?
He has agreed to compensate me with new terms under the original contract, to be paid after 4 drawings instead of 15. Is it always wise to just start over?
Not always. I've had contracts which started for email layouts and then had milestones added for web banners, for example. As long as the milestones for fixed-rate, or terms for hourly, are updated you're fine. In those cases it's helpful to make sure the change is documented in Messages in the job room, too. I like to keep track of job detail changes like that in Messages even if I'm communicating about the project mainly off platform with the client. But, if your gut tells you to be iffy about the client make sure you document, document, document. If you're moving toward a 4 drawing payment schedule just make sure your milestones indicate that and you'll be fine.
Thank You for responding, Melissa T
I also thought it was best to have such agreement discussed in Upwork's messages and not elsewhere so everything is documented. This is probably the strongest reason why I'm lenient with even considering to continue under the old contract because what was said is "saved". And as far as milestones, that price is less but what was agreed upon is in escrow. We just decided to work under a new contract for the rest of the drawings after the first 4 are completed.