Chicago Real Estate Investing Blog

By Mark Ainley

Developing Your Tax Strategy With Your Tax Advisor

There is a wise motto that it is best to be intentional, and estate and tax planning are no exception. Real estate investing offers significant tax benefits (discussed in my previous articles and more to follow in the coming weeks and months), and it is best to proactively craft ...

By Mark Ainley

Year End Tax Planning Considerations

The unpredictable calendar year of 2020 is slowly drawing to a close, and as we set our sights to greener pastures in 2021, we must finish up our tax planning for 2020. There are many important considerations that you, the real estate investor, will need to determine to execute y...

By Mark Ainley

6 Must Knows For Paying Taxes While House Hacking

We have talked about the power of househacking multiple times on the podcasts and why it may make sense for someone looking to get started in investing (and make sure to check out the Househacking Calculator under our Resources Tab). If you’re just getting up to speed, hous...

By Mark Ainley

Watch Out For Property Taxes in Cook County!

On multiple occasions, throughout this podcast, we've said you have to watch out for your property taxes.In February each year, the Cook County Treasurer releases new tax rates to the public, which are then used to determine the tax bill. Often the numbers are a mystery, but ...

By Mark Ainley

Three Signs That Prove a Community is Moving Forward

When deciding to invest in a community, there are three telltale signs that show that the community is moving forward and in the right direction. Ciere Boatright, Vice President of Real Estate and Inclusion at CNI shared with us three things to keep an eye out for. In t...

By Mark Ainley

How Tom Made 200k Into Millions Of Net Worth

The Tom that I speak of here is none other than my great podcast co-host Tom Shallcross. Tom was born and raised in the northwest side community of Dunning and 30+ years later he has not made it much further away into Jeff Park where he resides with his wife and 4 children. Altho...

By Mark Ainley

5 Tips When Investing In REO Properties

Many investors overlook bank-owned properties when looking to add to their portfolio. Savvy buyers who take the time to understand the REO process can uncover a huge opportunity for themselves in the form of great bargains. REO, or “Real Estate Owned”, is a term...

By Mark Ainley

Top 5 Mistakes When Using The BRRRR Strategy

Imagine you are attending a real estate investing networking event, and you overhear someone saying “BRRRR.” Chances are, they are not commenting on the temperature of the room, but rather, discussing this popular investment model known as the BRRRR method. So wh...

By Mark Ainley

Breaking Down BRRRR Strategy In Chicago

BRRRR is an acronym that breaks down the steps of a specific type of real estate investing strategy. This approach to real estate investing has become a popular strategy with investors who may not have the 20-25% down payment to invest in a long term deal or for seasoned i...

By Mark Ainley

Why Investing in Chicago Real Estate Makes Sense

I recently had the opportunity to speak with Emil Shour and Michael Albaum, both from Roofstock. We took the time to dive deep into investing here in the Chicago real estate market. This specific episode is perfect for investors who are looking to gather more information about op...

Find Out How Much You Can Charge For Your Rental