With a Conventional Loan you can buy a SFH, Duplex, Triplex or Quadplex with as little as 5% Down if it is your primary residence as long as you have the intention of occupying one of the units for 1 year after closing escrow.This is the strategy I have personally implemented and have assisted many of my investor clients in doing the same. 20% Down is also beneficial as it keeps your payment low but it does limit your ability of buying more real estate faster.i would be more than happy to discuss the different strategies with you over the phone or in person.

I asked when the other person will retire.  

I had a chat with them on the phone as i was curious about the funding.. but came to the conclusion that the down payment ( the client made to buy) was probably what they paid for the property and the seller carry back note was the profit.. and then the seller carry back note is sold to yet another investor.. who is investing for coupon money.   

I personally would never invest somewhere that could outlaw rentals.

.✅ More Control – You’ll personally handle tenant screening, rent collection, and property upkeep, ensuring everything is done to your standards.✅ Stronger Tenant Relationships – Being involved directly allows you to build rapport with your tenants, which can lead to better communication and longer leases.Cons of Self-Managing❌ Time-Consuming – Dealing with maintenance requests, late-night emergencies, and tenant disputes can quickly become a second job.❌ Legal Risks – Chicago has strict landlord-tenant laws.

All the add-ons are a la carte so you can definitely get a lot of value based on what you need.One thing I personally don't like is that when tenants pay rent, they are charged $1 per transaction for ACH use.

You'll want to put together a personal financial statement (basically lists of all your assets and liabilities) and have your tax returns ready.

The voucher is the most that Sec8 will pay for that person’s rent regardless of where they rent.  2) The second part of the Sec8 equation is the market rates for specific neighborhood’s and property types (SFR vs apartment, # bedrooms, # baths, utilities included vs paid by tenant, etc).

. $50 per bedroom, so a 4-bedroom house will cost you about $150~200consumables - bathroom supplies, kitchen supplies, beverage supplies: $20~30 per week, depending on how much you providewear and tear - towels, linen, kitchen utensils, some furniture: $1000~2000 per yearRepairs/replacement for things that guests break or steal:  $1000~2000 per yearAlso, if your personal use is less than 14 days a year, the entire property's expense is deductible against STR income, but if you use more than 14 days, then you will have to calculate the proportion of how many days it's rented out vs how many days you or your family uses. 

It is also worth noting that property management is often closer to 30% of gross rent for a short-term rental due to the much more intensive hands-on management compared to a typical 10% for long-term and as such, I agree with recommendations above that medium term rentals may provide the best of both worlds if you are able to tailor proximity to a local need, e.g. hospitals and travel nurses.Again, happy to relay my personal experiences in the area if you're interested.Best of luck,Patrick