This is a classic case of stepping over dollars to save pennies.

Classic CPA answer 😛 but it is in fact true.

However you do have the opportunity to look at a 1031 exchange which would indefinitely defer all of the tax on that $240K gain.Selling one larger property to use the proceeds to purchase several smaller properties is a classic 1031 strategy called a diversification exchange. 

Matt, If you are looking at historically built properties such as your classic bungalows, 2-flat and 3-flats in Chicago, many of those properties were built well before the modern zoning code was established.

I was trying to explore some of these ideas when I dived into the history of property search in a blog post I published, but I'm curious to hear more thoughts from the community here.That idea is too classic LOL Actually in the other thread I am asking similar tone.Here's my idea :1.

We have done this in all of the classic ways: driving for dollars, post cards, skip-traced phone numbers and cold calls, networking with local wholesalers, referrals and word of mouth, etc. 

This is a classic list it on the MLS, sell and move on with your life.

In my view, you're in a classic scenario that a cost-benefit analysis will solve.

Purchase price: $320,000 Cash invested: $6,400 Pretty surprised to find this deal, this was a classic case of someone listing a property that needed work, no one wanted to buy, it sat long enough on the market that people stop paying attention while the owner slowly fixed up.

I was referring to the "Mailing Online Classic" - which I don't believe has full color options for printing.