Well, I waited until the "right time" - after really not wanting kids at all, in the last year I have felt my feelings change through "I could live with having kids" all the way to "I want kids right now!". I strongly believe that for me personally it was best to wait until I wanted kids, that my own "right time". It would have been wrong for me to have kids just because DH wanted them - we both agreed on that.
I am now 34, and finding it hard to conceive. That's the problem I guess - no couple knows how hard or easy it is going to be to conceive before they actually start trying. You could wait until "the right time" and suddenly find you've left it a bit late and things are difficult. Or you might find you are super fertile and get pregnant first cycle!
Another consideration is how many kids in total do you want? How far apart in age do you want them? How old will that make you when you're ttc number 2 or 3? You're at a good age now in your late twenties, having kids into your early thirties should not be too much of a problem, but take heed of all the medical advice about ease of conception and chances of abnormalities after the age of 35.
It's good to be aware of your financial and work situation, but think also about "worst case" scenario - if DH's freelancing didn't work out, would he be able to go back into full time employment? Or would you be able to survive on your salary alone?
My DH runs his own business from home, and we need my salary to keep bread on the table. So our plan is for him to look after the baby when I return to work. However I'm not sure yet how much work he'll be able to get done with a small baby in the house, and we may need to live without his income totally. All things we'll just deal with as and when they happen.
This is turning into quite a long post, I guess my point is you have already made the largest decision - that you both want kids. All the remains now is sorting out the details of when. And in that case, I think your DH is right - there may never be a "perfect" time. Think about the big picture. Also think about how things would be if you discovered you were pregnant tomorrow - it may not be as scary as you think.
I hope some of this helps in some way!
Hugs,
Artoo.