It may be a small chance of getting caught, but still a chance which makes it not worth it, in my opinion. 

.🎯 Your 6-Month Timeline:Month 1: Foundation (5-7 hours/week)Morning routine: 1 hour daily market researchEvening routine: Deal analysis practiceWeekend: BP forums & networkingKey Goal: Analyze 10 deals on paperMonth 2: Education (8-10 hours/week)Complete 1 RE courseJoin 2 local REI groupsSchedule lunch breaks with agentsKey Goal: Build your initial power team listMonth 3: Systems (10-12 hours/week)Set up deal tracking systemCreate document templatesEstablish banking relationshipsKey Goal: Ready to make offersMonth 4: Lead Generation (12-15 hours/week)Drive neighborhoods after workWeekend open housesSetup automated MLS alertsKey Goal: Generate first 5 qualified leadsNow, the Owners and Brokers you deal with may not enjoy this, but you can certainly "practice" making offers.  

If its a Class C I'd go for a more affordable unit, there's no point in putting in more money than you have to. 

Here are some practical steps and strategies to consider:## Single Family and Small Multifamily HomesWhen looking at single-family and small multifamily homes in northern Illinois and southern Wisconsin, make sure to analyze the local market trends, rental yields, and property appreciation rates.

I don't think its as easy as people make it out to be. 

But enough to make to do all the cosmetics along with a few major items like HVAC, appliances, etc.

Make sure you have that addressed just from a liability standpoint. 4) You could also look into a mid-term rental option with traveling nurses if you think the unit is truly rentable. 5) AirBnB restrictions have gotten much stricter as well in general in Chicago, so make sure you are on the right side of those if you put your unit up since you are required to register with the City.

Quote from @Michael Overall: Good day, If an investor has 10 rentals and wanted to over time sell them and put the money tax free from a 1031 toward a large purchase is there a process to do that? 

Take a bit of that money and invest in learning - go to meetups and the many events that take place related to investing in the city - some for free and some paid.

When making offers I want to utilize the standard 70%-ARV-Profit formula.