So when you build your pocket neighborhood, which is an interesting concept, what's to stop an undesirable person from moving in.

Once the year passes you can move out, rent and repeat or try something else. 

Everything on my side was set to close, and then today the seller is refusing to close on Monday as they have not moved a few pieces of furniture they were supposed to get movers for.

It’s exciting to hear about your plans to dive into this field, and Chicago is a fantastic market to explore once you move there.It sounds like you’re on the right track with your interest in House Hacking, Mid-Term Rentals, Short-Term Rentals, and the BRRRR strategy.

Spend a little more money than you might have been planning to, buy in a better area (i.e. not a “turn key” 100k house off the mls), and self manage.

@Chris Mahoo Even without qualifying for Real Estate Professional Status (REPS), long-term rentals offer key benefits like depreciation deductions over 27.5 years, deductible expenses (e.g., mortgage interest, repairs), and up to $25,000 in passive loss deductions if your MAGI is under $150K.

Everyone will tell you it’s great to get started early, or you can just move after a year, but in the current environment in our region the rent your property will generate after you move out will likely be less than your mortgage, if you are tied to the area and feel confident you want to stay in whatever property you buy for 3-5 years go for it, if you want flexibility rent and throw that money into and index fund. 

I am a resident physician in dermatology, during  medical school I bought a property in Denver with an Interest rate of 2.75% (COVID rates lol) with the goals of renting it out when I moved onto the residency.

You'll have to keep me posted on your next move! 

But I found out my neighbor who moved out to help her father, is planing to rent her place next door to me.