Similarly, the sale ($575K) minus your adjusted basis determines your capital gain.You may qualify for the primary residence exclusion (up to $250K single/$500K married) if you lived there 2 of the last 5 years.

I have three rentals and my primary residence here in Springfield Illinois. 

However, you can defer taxes under §1033 involuntary conversion if you elect to reinvest the proceeds into a similar rental property within two years (three years if the government condemns the property or threatens to do so, and four years for a principal residence in a federally declared disaster area).To reduce taxable gain, consider:Electing §1033 treatment and reinvesting the full $300K into a new rental property to defer taxes completely.Partial reinvestment, where only the portion not reinvested is taxable.Properly documenting all replacement costs and property details to ensure IRS compliance.Using cost segregation on the new property to accelerate depreciation and offset future taxable income.Since the §1033 election must be made, consult a tax professional to ensure compliance and maximize deferral benefits.This post does not create a CPA-Client relationship.

I'm going to exclude my personal residence from this because I don't view this as an investment, I need a place to live.Excluding my primary residence my current breakdown is 47% real estate 53% stocks/cash. 

Investment Info:Single-family residence fix & flip investment.

You might decide that you absolutely want to own your own residence there and I assume you can afford it since you already own properties elsewhere, likely in beautiful Hawaï.

Primary residence is paid off. 

This defers capital gains and depreciation recapture taxes on the sale of your fourplex.After converting it into your primary residence, you may qualify for the primary residence capital gains exclusion ($250K single/$500K married), but only for appreciation after the conversion; gains from the rental period remain taxable.

When purchasing a small multi family property as a primary residence.

Investment Info:Single-family residence buy & hold investment.