Trade up in the same market- Are my parents right?

I bought around peak and would like to trade up from my studio sometime in the next few years (several quality of life reasons, nothing urgent). I know real estate is always a gamble and it does seem like things have stabilized a bit. But big picture, I'm betting that best case scenario, prices are flat in coming years or decline modestly. If I cut my losses and sell now, I would keep most of my... [more]

I bought around peak and would like to trade up from my studio sometime in the next few years (several quality of life reasons, nothing urgent). I know real estate is always a gamble and it does seem like things have stabilized a bit. But big picture, I'm betting that best case scenario, prices are flat in coming years or decline modestly. If I cut my losses and sell now, I would keep most of my 20% down after closing and lose around 40K renovation/improvement costs I put in. I could get a better 1-2 year rental (for close to my current carrying costs), and keep my cash safe at 1% until I'm ready to buy more. I'm not comfortable trading up in this bipolar climate, and would like to build up my reserves for another year or two. And if meantime prices fall, the bet pays off. My parents don't agree: you should always buy and sell in the same market. If your studio loses X amount, then a 1 bedroom loses even more. Don't think you can time the market. You might end up selling low then buying high in a seller's market. If you're not ready to trade up, then stay put til you are. I argue that the greatest risk is to wait too long to sell, lose too much equity, and not have enough left to trade up. I don't think prices jumping back to peak is a real risk right now. My parents are often right... but are they? [less]