I start at $5K minimum no matter how crappy the domain and go up into 6 figures based on individual circumstances.
And just because the .com sold for $3K, don't think that means can't get more for the .ca.
Of my last 4 sales, 3 were 2-word .CAs (one was a geo) and the average price was in the 5 figures.
My opinion is that if you're not willing to spend at least $5K for your domain/brand, then you're not very serious about your business, in fact I'd call it a hobby, not a business. I flat out tell potential buyers that the price is set higher to specifically ensure that the domain ends up with the right buyer, not just the first buyer that comes around that has $500 in their pocket. If you sell cheap, you have to sell a lot, and then you have to buy a lot. I say treat your inventory like the one-of-a-kind items they are, more like an art gallery than the dollar store.
I'd also rather have 1 sale at $10K than 10 sales at $1K. One obvious advantage is that you still have 9 other domains to sell rather than zero. And you can't get big sales unless you've got the determination to say "no thanks" to a lot of offers. I push the buyers and find their limit, sometimes I push too far and lose a sale, but my experience says it works out better for me in the end this way. In fact if they counter my initial price, I don't counter back by lowering the price, I counter back by offering a payment plan. And if they say they don't need a payment plan, then I say I guess budget really isn't the issue is it? Of course I say it as nicely as possible. Definitely be very courteous and respectful, treat them like business people. Lately, I've used chatGPT to remove the snarkiness of the replies I want to send, to something much more diplomatic and likely to lead to a constructive conversation.
Of course pricing depends on the domains you're investing in though. Maybe a better way to think of it is, get a good return, then slowly averaging up the quality of domain you re-invest in.
These are the multples I've sold my last 10 domains for (average hold time 7 years). Note that I didn't factor in holding costs, just the multiple of sale price vs acquisition price. 170x, 60x, 1000x, 123x, 83x, 385x, 138x, 138x, 435x, 160x
Obviously its easier to get a higher multiple on a cheap TBR domain than one you spend > $500 for. On the other hand, holding costs erode that multiple quicker on a cheap domain than on an expensive one.
That being said, I personally am not usually thinking of the ROI when I price, unless its a domain I spent a lot on to acquire. Sometimes I'm willing to take a smaller multiple to get out of domain I overspent on. Some investments are just better than others and time has a way of pointing that out. I'm mostly pricing based on the popularity of the word, its length, ease of spelling, memorability, connotation and brand suitability, comparable sales, independent valuations, etc, The more you do it, the more of a gut feeling you get for reading those signals and pricing accordingly.
And then of course there are the personal factors. If you're struggling to pay the renewals, do what you gotta do to make a sale. And when you do make a sale, maybe pay for some renewals in advance. It never hurts to be prepared for a bad year.