Opportunity with bad timing?

Hi investors

I have a dilemma and would love your thoughts…

Young family with a toddler and infant. We are in our 40’s with low paying jobs. We own a 2 bed unit, purchased for 1.35 during the peak. Now worth about 1.1.

A friend owns a house worth about 1.3. Nearing retirement age, casual employment.

She has proposed we each sell our properties in 2020 and buy a dual occupancy house together. Separate living quarters with a shared yard.

It seems like terrible timing given we’d be selling at the bottom of the property cycle but also possibly a great opportunity to buy a house whilst we are still of working age.

We would of course buy in the same market which would hopefully offset our losses.

For what we’d be able to sell for, what we hope to buy (dual occupancy house) and where we’d want to buy (Eastern Suburbs beaches Sydney), it’s probably unlikely.

Can anyone think of a better plan?…