I bought it off market at a great deal with a conventional mortgage as a primary residence with the plans to rent it after the 12 month period has passed so I can legally rent it.

They honestly know what they are doingThe true way to know if someone is reputable is if they know their guidelines, can call you out if you are being unrealistic, and are quick to kill a deal rather than piece gum together and see if it will pass.

All a landlord has to do is buy, hold, do the minimum the city requires to upkeep the property, and let time pass.

Also, considering that new propositions may pass that would limit/restrict future increases.Look forward to hearing from landlords, investors, previous/current renters and anyone else to help me determine what to do. 

Hello all,I just passed my residential leasing agent exam and am looking to work as an agent in Chicago, IL.What companies are recommended for a starting out agent?

If Planning does determine the existence of your ground floor unit, it will require you to legalize the unit through the existing Planning code process assuming zoning supports the third unit OR using the new ADU program making your fast track condo conversion a passing dream.With regards, to some of your latter comments and questions:1) Any un-permitted work (including corrections) is not a good idea as a quick compliant from a neighbor can bring an inspector knocking on your door with a NOV especially in the current environment where everyone is SIP.2) Legalizing existing constructed spaces can be hit and miss based on the inspector you get.

Do that every year and you can use the additional revenue to deal with these kinds of situations when they come up.Also, if you live in a regulated area, you may want to look up your right to pass through costs when you have to do a major repair.

Regarding Floor 3 leak, I am entertaining a full roof replacement but may Karnak myself first since that leak could not be reproduced on my test and appeared after a heavy rainfull. water ran along a joist. 

You could borrow a second against the $400k of equity in your property - and accept short term negative cash flow to earn a lot more on the great deal you don't want to pass up.  

People move, they pass away and they change their email addresses every day.If you do telemarketing, you can expect that nobody will answer their phone and maybe 50% or more of the phone numbers are no longer in service.