It just happened that im in the process of purchasing 2 properties this month. 1 is a rehab, that I plan on keeping for my self for a bit then selling.. the other is an invest property non owner occupied thats a 3 familyThe rehab I need to purchase out cash 105k and another 15k-20k to repairThe rental property I need to put 25% down and closing is around 70kSo I need 175k to purchase and another 30k to repair both properties I have 90k in liquid in a savings account,  230k in a 401k made up of the funds and stock and about 330k in my companies stock account..My plan was and not sure if this is the smartest way .. hence why I'm asking here!

I know that renting up your investment can be one of the most confusing and nerve-wracking parts of the process (especially in a place with as much bureaucracy and legal hurdles as Chicago) and am more than happy to talk with anyone about that.

Hi Michael-Great question and an important skill for investors to understand.I recommend the ABC's of Real Estate Investing by Ken McElroy and Ken's YouTube Channel.If you are an investor, I recommend finding and using a good property manager for your properties as soon as possible to maximize your return on investment and make owning as passive as possible.A good property manager is a key part of your real estate investing team.Get them involved early in the underwriting process of a potential acquisitions and the planning for adding value.To Your Success!

Once you start talking to more people in the niche, you'll get a better idea of the process and whether or not you want to pursue buying in this niche. 

I guess the trouble I'm having is figuring out how and when to apply that criteria in my process.

To directly answer your question- if your PM hasn't already taken action, fire them, hire an attorney to start the eviction process and start interviewing new property managers. 

Going through the FHA process has been a headache for me because the underwriter is asking for a lot of information for each of the properties including the signed lease agreements for all tenants.

You need to ask for all information about the tenants right at the beginning of the application process. 

During this process I've run across a property in Birmingham that has some good numbers "on paper."

At least the process here will be harder than just a city council getting together and banning it overnight on a whim.