There’s no singular answer to your question. Different sellers do it differently. Some sellers increase their prices as soon as they get promoted to a higher level. Some sellers raise their prices gradually over a long period of time. There are others who constantly modulate their prices based on the sales/traction they make/have.
You need to do what’s best for you. You could raise your prices and see the impact it has on the number of orders you receive. You will have to experiment a little to find out what works best for you.
Of course! It is only logical that most buyers would prefer the cheaper price. Why pay more when you can get the same thing done for lesser, right?
But, if you were undervaluing your gigs and selling them for lesser than what you/your buyers think they’re worth, your buyers (who realize your potential and love your services/products) may not mind the increase in prices.