DOOFUS | Buying For Investment Or Upsizing

[Ran Iarovich]

Hi everyone,

I stumbled upon a dilemma about what I should do with my current property and need some thoughts as to what I should do. I currently own a property that is valued at around $1.2 mil. Since I bought it in 2010, I have made sizeable profit on the property. The $1.2 mil price point comes after heavy remodeling for the kitchen, fixtures, heating, and more. I have probably spent anywhere from $150k - $200k in total repairs. I'm also a frequent short-term stock trader but want to diversify to real estate. My reasoning is that I want to pay less taxes because I'm in a very high-income group and also to get more expected returns. 

Now here is my question. Considering the time needed to manage a property, the tax benefits, and the overall returns, should I buy a property that would cash flow as a rental and continue to live in my residence or upsize into a new property and turn my current residence into a rental? Another option would be to sell my primary residence and be able to afford something much bigger. I'm very worried about my tax payments and want to make sure that I can write off as much as I can depending on what I do. 

Sorry if my post seems a little obscure and lacks information. I'm very new to investing in real estate and still educating myself on the proper vocab.