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.

[Frank S.]

Originally posted by @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.

It is not difficult to time the market, it's impossible. 

2014, there is a market crash coming
2015, there is a market crash coming
2016, there is a market crash coming
2017, there is a market crash coming
2018, there is a market crash coming
2019, COVID!! there is a market crash coming
2021, Construction will tank! there is a market crash coming (didn't happen)

You get the idea.  One day they will be right, no one knows when

Your home is not an investment, it's a personal consumption choice. Do you order a latte in Starbucks or a cup of Joe at Dunkin, same goes for one's home. I wouldn't, it's a pain to find a home.