Sell my current home, rent and wait for the the market to drop?

[Oscar Martins]

Looking for a bit of advice. I have been living in a single-family home (my primary residence). I purchased it three years ago for 150k with the intent of flipping it but decided to make it my primary residence. I put in 50k of repairs over the last three years. The value of the home is now worth 450k - 475k.

My question is, should I sell my current home, move into a rental where my rent will be $5,000 higher per year than my current expenses, wait to see if he market drops a bit and then use the proceeds to purchase a multifamily home in 2-3 years. I also know its very difficult to time the market. Thanks in advance.