Depending on where you are looking, inventory for 1-4 units can be a challenge as a lot of the NW suburbs are all single family homes unless you are further NW like Rockford or Elgin or something like that. 

This means you can buy a SF and convert or build a separate unit.

If you plan on selling the property always try to leave at least one unit vacant this way you allow for more types of buyers like house hackers or investors.

It is improving, meaning sellers and builders are facing a little more competition, but there is still a shortage of housing units in the region. 3) Rental prices are strong and single family homes and townhouses rent very quickly.

Is there a legal limit on how many rental units/tenants we could have on one single family lot?

All you get is what you can export/import via CSV file:(We use Propertyware, have experience with Buildium, and have played with Appfolio and RentManager.Buildium is for smaller companies.The other three are tied, the differences being how much automation & customization you want to do.If you don't see yourself growing beyond 150 units, go with Buildium.If you're not very techy and plan to grow over 150 units, we'd recommend Appfolio.If you're techy and plan to grow over 150 units, we'd recommend Propertyware or RentManager.Of course, schedule some demos, take GREAT notes and them make your decision.FYI - there are MANY new options on the market, RentRedi, TenantCloud, Apartments.com, Hemlane, Rentec.

I have a friend who has one in Florida where he doesn't have to do any repairs or maintenance to his unit.

If you are willing to sacrifice part of your life style, you can always consider living one room/unit of the house and rent out the other vacant unit out to lower your monthly mortgage payments!

.$379 Insignia 70" F30 4k Fire TV - https://www.amazon.com/All-New-Insignia-70-inch-Class-NS-70F...Not a bad TV if you are looking for a larger unit.

@Paul BogardTo rent out multiple bedrooms in Philadelphia, understand zoning regulations, consult a knowledgeable real estate agent, hire a property manager, and consider multi-unit properties, student housing, and co-living spaces.