love that quote. my opportunity fund is in one of my high yield savings. i have separate retirement accounts (through work and ira), separate taxable accounts (stocks/index funds), separate emergency fund, and a separate opportunity fund for things i can use if i want to buy real estate, fund one of my side hustles, buy stocks/index funds if the market crashes, use for vacation, etc. i keep this fund separate from my emergency fund both in high yield savings accounts. i need my opportunity and emergency funds to be liquid so i don't mind only getting a 2.xx% rate. happy to discuss further as personal financing is one of my big passions. hope that helps.

Look at your current taxable income and see where that lands you. 2009 tax rates.

We’re hoping to do more of this in 2020 now that our investments are generating some more significant taxable gains. 

This is a great school district and we are thinking we might want to move back here when our newborn is of school age (in 5 years), which is why we are leaning towards renting it so we can return.3) In looking at tax benefits of renting I can't seem to get my taxable income to be less than the actual cash I'm making in a year.  

The increase of the basis will help you minimize the taxable gain when you eventually sell the house.2) Improvements made on the rented side will also be added to the basis, but you can depreciate the improvements on the rental side and deduct depreciation against the rental income.

Making money is taxable; saving money is not.I highly recommend reading Set For Life (a BiggerPockets book) by @Scott Trench.

@Patrick McCandlessYou can do this, but the gain is likely so minimal as to not be beneficial.When you take a distribution from an IRA, the amount distributed is taxable income to you.  

Free money from your company, as well as reducing your taxable income.

Income earned by a trust is taxable by the IRS and the top tax bracket is hit much earlier than for individual income. 

More companies may allow employees to work remotely, which will reduce demand for office space and lower the value of taxable real estate.Then there’s the stock transfer tax proposed by state Sen.