I’m going to cross post this in a few places and to be clear, I am NOT talking about software or a bookkeeper that specializes at any of the following:bookkeeping for taxesrent roll and property managementproperty purchase assessmentrenovation budgets and build managementtraditional stock market investmentsbusiness managementpersonal financesI am looking to take information from all of the above areas and create a holistic cash flow, net worth, short term and long-term automated projection of EVERYTHING all at once.

I’m going to cross post this in a few places and to be clear, I am NOT talking about software or a bookkeeper that specializes at any of the following:bookkeeping for taxesrent roll and property managementproperty purchase assessmentrenovation budgets and build managementtraditional stock market investmentsbusiness managementpersonal financesI am looking to take information from all of the above areas and create a holistic cash flow, net worth, short term and long-term automated projection of EVERYTHING all at once.

It is never really justified if they are a generalist, if they specialize in something like trust creation, company structuring etc. then it might be worth something.

You don't need an agent to buy or sell land (I almost never use them), but depending on your level of comfort with the process, it might not hurt if you can find one who specializes in land transactions (hint: most agents deal with homes and dwellings, and these are not necessarily the most qualified people to advise you on vacant land transactions - as land deals have their own unique set of issues).2.

From what I understand, Chicago Zoning Laws permits the use of the space for group living but may require a special permit.

make sure they are multifamily insurance specific or specialized in some way.

It's an ordinary home in an older community of older homes, nothing special.

Geoffrey,I recommend finding an accountant who specializes in real estate taxation over one that is local. 

I also made sure that I connected with a broker/brokerage that specialized in investments and investors (I was thankful to find a Brokerage that is also a Property Management company), which also helps me tremendously in my growth as an agent and investor. 

If they want some special fridge the tenant should purchase it themselves.