This would be my first investment property so I have a few questions.1.How long is the process to get approved for section 8.2.With the selection process am I able to go through the same steps as I would to select ordinary tenant.3.Are most people actually getting an inspection every year like it states on the website.4.

Before the alderman will meet with you, many ask for the plans with the 4th unit, so you will need an architect first and foremost.This process can be done without an attorney, but it is 100% up to the alderman to approve you and it can be a long process with limited success. 

Do I treat this as a normal purchase and get funds, pre approval, contact agent? 

For example,If Bob and I agree to a similar partnership as mentioned in Brandon's example, Bob applies for the loan solely, is there a way in which we can both hold liability for the debt? Or

As she was leaving I asked her to text me when she was ready to drop off her application, so I could meet her in a designated location as I do not not like applicants to know where in the complex I live until they have been approved to move in. 

When the structure is serviced by an individual sewage disposal system, the applicant shall have the existing or any new system approved by the department of environmental management.

If you decide that renovations went faster than expected and want to move out in 8 months, you'll need to refinance out of the FHA loan first.3] Lenders approve you, personally, based on your debt-to-income ratio.

Biggerpockets also sells a Landlord Package that includes a lease and several other forms, specific to your state, written by actual investors, and attorney approved.

Also, you could check out AirDNA which has great stats for short-term rentals.You do have to register with the city of Chicago, Airbnb makes it pretty simple but as @Brie Schmidt mentioned there are specific requirements to get approved. 

(I recently bought a home and my pre-approval was only that high) So I realize even if I do get hard money up front, I wouldn't be able to refinance after a year because of that.