Is it legal to do an off-market transaction straight through the title company without using the agent? 

There are companies/agents that specialize in what you are looking for.  

I just recently found out that my company is closing mid summer.

First, I'd try to find why the water is doing that as you can replace the siding, but if the water is going to keep doing it, you will have that problem again.If it is isn't a condo, I'd talk to your insurance company.

I am a first time homebuyer looking to house hack in Chicago and I have an almost 800 credit score, but I don't really have much saved up beyond my emergency fund for a down payment.

Many OOS investors set themselves up for failure because they don't invest the time to ACTUALLY understand:1) The Class of the NEIGHBORHOOD they are buying in - which is relative to the overall area.2) The Class of the PROPERTY they are buying - which is relative to the overall area.3) The Class of the TENANT POOL the Neighborhood & Property will attract - which is relative to the overall area.4) The Class of the CONTRACTORS that will work on their Property, given the Neighborhood location - which is relative to the overall area.5) The Class of the PROPERTY MANAGEMENT COMPANIES (PMC) that will manage their Property, given the Neighborhood location and the Tenants it will attract - which is relative to the overall area.6) That a Class X NEIGHBORHOOD will have mostly Class X PROPERTIES, which will only attract Class X TENANTS, CONTRACTORS AND PMCs and deliver Class X RESULTS.7) That OOS property Class rankings are often different than the Class ranking of the local market they live.Class A is relatively easy to manage, can even be DIY remote managed from another state.

I called my insurance company to try to get medical insurance coverage and they referred me to a broker who specializes in this through the marketplace.

I'd like some reviews on property management companies in these cities as that will be a big deciding factor for me since I will be an out of state investor and this will be my first investment!

We can help you out with offmarket aquisition and Property Management in Cincinnati , give me a call to see if we have answers to all the woes you had with your previous PM companies you used , or if you are new to investing in cincinnati we can start from basics and help you put as well 

Is it to our advantage to mention that we're just a regular couple, not a company?