Hey Hey @Veronica Mitchell - The most simple advice is to follow the CTA trainlines.I personally love the South East Corridor of Chicago which has Bronzesville, Kenwood, Washington Park, Hyde Park, Woodlawn, and South Shore.That area will continue to be gentrified because you have the lakefront and CTA trains.Others mentioned NW along the Blue and West along the Pink, Green, and Blue lines.

Still can be very beneficial for a new investor but personally I think not as good as a service as they had with their exclusive listings where they had inspections already done, rent rolls available, and you can complete the entire offer/acceptance via their platform rather than being handed off to an agent. 

Also, you don’t need a business license just to look at properties, but if you buy a bigger property, like a multi-family unit, you might need a certificate of occupancy, depending on the local rules.For business trips, most expenses can be deductible, but if it’s part personal and part business, you can only deduct the business portion.

I'm going to reiterate what's already been mentioned above, but I'm going to actually give you examples of why it's relevant to you to find a U.S. tax professional.1 - You're going to need to file U.S. taxes once you have property down here, there's federal filings, state filings, and sometimes local filings too2 - Tons of tax treaties between the U.S. and Canada that are easy to miss and can cost you a lot of money (important one with rentals - effectively connected income - if the professional you talk to doesn't know what this is, run away)3 - The amount of days you spend in the U.S. needs to be tracked and if you go over a threshold, all of your worldwide income could be taxable by the U.S.4 - Selling real property means up to 15% of your sales proceeds might not be available to you for years (FIRPTA)5 - Lots of nuance at the state and local levels, which both want to take as much money from you as possibleMain takeaway here is that you should find a U.S. based tax person.

You’re going to be personally sued no matter the cause of the loss.

@Reyna AyalaI personally feel this is overkill.

I have personally been the guy who hasn't pulled permits and got caught...by far one of the worst experiences of my investing career.

We take a "whole person" approach.

There's a common belief that your tax person should also be an investor themselves.

If you want to think about it as a math problem, it’s all about where you put your time to maximize returns while also factoring in what you enjoy doing.Picking the MarketI’m the kind of person who gets analysis paralysis.