You're gonna need to put the work in, dedicate most of your days to your goals, select your priorities very wisely, and be disciplined enough to work on them.

Hey @Daisy Ruiz, choose another area. 

However, if my goal is to house hack this for a year and then move into another house hack, should I be looking to at least break even accounting for all expenses mentioned above?

Any asset you buy that provides income is an investment.Whether the home in your scenario is considered an investment or not really boils down to your goals with the property, but it also doesn't really matter.

It all comes down to your goals and if it makes financial sense as to which direction to go

Here’s a breakdown to help you navigate your first deal, incorporating advanced strategies, including 1031 exchanges, to attract a broader range of investors.Neighborhood Recommendations: Chicago offers a diverse range of neighborhoods for different investment goals:Wicker Park & West Town: These areas are known for their strong rental demand among young professionals and offer good potential for cash flow.Lake View: Ideal for attracting tenants who want to be close to downtown while enjoying local amenities.The Loop: A prime location for high-income renters, making it an attractive option if you’re planning to house hack and generate a steady stream of rental income.Property Types: Opt for properties that align with your investment goals.

So my goal is to put 5% down on a conventional for a mfu, then use a pml or hml for the renovations.

Congrats on your growing business and best of luck in whatever you choose!

My concern is the markets they're choosing to purchase into at the moment.

I personally choose to utilize the traditional LLC for my first few properties and it has treated me well.