Thanks for the mention, @Jonathan Greene!

That’s  Like saying nobody in their right mind would own an investment property in Illinois for various reasons that don’t need to be mentioned.

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?

If you wait for a storm , you will also be waiting for a roofer to do the work . 

#3: If it’s an on-market deal as mentioned in #2, does that change who I have in my corner?

Chris showed couple of other properties that they invested in, renovated and waiting on sale.

Others 15 yrs, etc.So we depreciate a portion of the asset costs faster.We do the study and get dollar amounts assigned to different parts and different schedules to front-load depreciation.Now you can get 5 or 6% of the value as a deduction in the early years...But wait... there's more.Bonus depreciation allows you to deduct a certain percentage of cost in the first year an asset is put into service.Anything that is on a schedule of 15 years or less...So the doors, sidewalks, HVAC, walls, latches, curbs, security, gates, etcA % of this stuff goes in Yr 1.For years 2015 through 2017, first-year bonus depreciation for these items was set at 50%.It was scheduled to go down to 40% in 2018 and 30% in 2019, 0% in 2020.But then the Tax Cuts and Jobs act moved this percentage to 100% from 2017 to 2022 and 80% in 2023 and 60% in 2024.Its not uncommon to allocate 30% of an asset cost to items that can be depreciated on a 15 year or faster time frame.So now 60% of that 30% of your asset's cost can be depreciated in the first year, excluding land.Pretty great.This is how real estate owners, investors, and operators make millions and pay very little in taxes compared to W2 employees.They pay even less and can offset other types of income if they are an RE Pro.

I remember him mentioning it multiple times in the podcast, but I can't remember the specific book, can anyone help me out here?

That bathroom you mention may have to be torn apart and redone, it depends largely on the individual Inspector that you deal with.I would go to the County/City Building Dept counter and talk to them in person.

Should we wait to put in our offer??