A 1031 will help defer taxes, but you will lose the income source on your triplex 

It’s not as fun when you lose half of your home value, such as between 2005 and 2009.  

I know you cant lose too bad if you find a great deal and hold but is anyone else getting stuck just waiting for the drop that may or may not happen haha.

If your friend subdivides and puts homes on there, they will either gain or lose value based on the current market. 

This is literally the blueprint to failure and losing all of your money.

I didn't lose money, but on paper it shows a loss (due to accelerated depreciation on the cost seg). 

I didn't lose money, but on paper it shows a loss (due to accelerated depreciation on the cost seg).

Hey @Kayla CarsonI am actually investing in the same area as you and also possibly doing the same strategy.The way I look at it when it comes to house hacking is whatever the dollar amount that's left after all expenses, if that figure is more than my current cost of living, than I am losing money.

@Heidi M.This is a non-tax related thing to consider as you lose 10%-15% in value when you sell a home and acquire another home.What is missing in the current home that you are looking to get a new home?

If you sell the home, expect to lose about 10% of the value of the home in fees/costs.6% to realtor commissions, 4% in other closing costs(Transfer taxes/title costs).There may also be income taxes as a result of the sale.