The Do-Over

This post is from Kevin @  Kevin is a co-founder @, where he helps consumers manages their finances and find the optimal way to get out of debt. .  This is guest post is part of a blog swap for the Yakezie, answering the question “If you had one financial do-over, what would it be and why?”.

I usually look on the brighter side of things.  There’s never an incident where I wish I could go back in time and change things.  Everyone will eventually make mistakes, but it’s up to them to learn from these mistakes and make sure it never happens again.  However, if there was one moment in the past I could change, It would be not buying a house straight out of college.

Throughout my college days, I have been fortunate to have saved up enough money for a down-payment on a house.   That’s not enough to maintain debt-free living. I worked with several internet gaming companies and acted as an affiliate for them.  I saved up around $25,000 and decided to buy a condo with my brother.

I thought it would be cool to own a condo in the city.  I was really looking forward to turning this new place in a bachelor’s pad.  This was probably the worst decision I’ve made.  I always believed that it was better to buy a property instead of renting one, since some of the payment would go towards paying down the loan.  Of course, I realized that this wasn’t the smartest of ideas.

Here are some reasons why I regret it:

  1. Property Taxes:  Property taxes in Chicago are one the highest in the nation.  For a $320,000 property, annual real estate taxes were roughly about $5,800/year.  Property taxes usually go up every year, it can be difficult for some people to maintain these payments.
  2. Valuation:  Thankfully, the property only decreased 10% in the past 2 years.  It’s not as bad as some areas, but the timing to buy a property was poor.
  3. Cost:  Buying a property involves more money to spruce up the place.  New paint, new appliances, new floors, etc.  Most of us won’t get a free appliance from the government.  Many homeowners have to put in extra care of the property, so when they sell it, it’s still in great condition.

Looking hindsight, I definitely wish I rented instead of owning a home.  In this day of age, I think most people can make the clear argument that renting is worthwhile to look into.

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    1. Property taxes and municipal finances are not something that was thought about much when purchasing a house, but now it is something that needs to be considered. Many property owners may be expected to pick up the slack in tax revenues.

    2. Buying isn’t always the best financial move. Sorry you had find out the hard way, and hopefully you recoup your investment soon!

    3. Buying right out of college can be tough, because what if you needed to move for a job or something? You would be trapped there until you could sell.

    4. We have been in a very tough real estate market over the past few years. Although it’s tough to see the valuation decline a bit, over time, living in a major mkt like Chicago, you should realize some decent appreciation. But I do understand your wish for a do over.

    5. Property taxes, valuation, and costs are definitely things to consider when deciding upon renting or purchasing a home. It is important to take each of these aspects into careful consideration when establishing a budget in order to have long term financial success down the road. While it is nice to plan on having a home several years later, if there is one thing I’ve learn over the last year its that finances can change quickly. Planning an adequate savings and avoiding putting a majority of your income into a living arrangement is the lesson I wish I could have learned a little earlier on.

    6. This comes at a perfect time when I am considering renting versus buying. There are just so many costs to figure in that unless you have a large down payment, the cost of buying is worse than renting for a while. Maybe even the first 5 years. I’ve decided to save up 40% of the home value and put 20% down and save the rest for repairs and emergency cash.


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