Chicago Real Estate Investing Blog

By Mark Ainley

5 Best Practices for Keeping Accurate Records

This is one area that real estate investors often bemoan and dread before tax time. However, it does not have to be that way. There are simple, practical solutions that you can make to keep better records. In this article, I’ll go through why keeping detailed records are im...

By Mark Ainley

The Best Retirement Account For The Self Employed

While it is increasingly more popular to become an entrepreneur, there also needs to be some consideration for setting yourself up for future growth. In traditional W-2 jobs, there are 401(k)’s that function as excellent retirement vehicles with some restrictions. When you&...

By Mark Ainley

Seller Financing Explained

Do you understand how seller financing can benefit both parties in a transaction? Many investors are aware of the benefits that seller financing provides the buyer. However, few buyers understand how advantageous seller financing can be for the seller from a tax-perspective. The ...

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...

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