We have been waiting for rates or prices to fall before buying, has anyone actually timed it and come out ahead

The other side of it. We waited eighteen months, mostly by accident because of a job move, and bought in a market where nothing was selling and we were the only offer on the table. We got a reduction and a seller who paid for half the repairs on the survey. So yes, waiting can work, but it worked because we were ready to move fast when it got quiet, not because we predicted the quiet.

I would be careful with the marry the house, date the rate slogan that always comes up here. Refinancing later is a possibility, not a plan, and it depends on rates, on your income at the time and on the property still valuing. Buy something you can afford at the rate you are actually offered, and treat any future refinance as a bonus.

I waited three years for a correction that did not arrive in my city. Prices went up, rent went up twice, and my deposit grew slower than the deposit requirement did, so I ended up buying a worse flat than the one I passed on. The part nobody tells you is that waiting is not free even when nothing happens, because you are paying rent for the privilege of holding the option.

Run both levers through a payment calculator before you decide which one you are waiting for, because they do not move the same way. A meaningful rate drop changes your monthly payment a lot and often pulls buyers back into the market, which pushes prices the other way. Waiting for both to improve at once is waiting for a thing that rarely happens.

Disagreeing with the framing rather than the answers. The market question is unknowable and everyone in this thread including me is describing one draw from a distribution. What is knowable is whether you will still want this house and this city in five years, and if the answer is yes then the timing question shrinks a lot.

You cannot rent the house you want and buy it later at today's price. Decide on the life, then negotiate hard on the price.