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.

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.

I am 50 years old and have decided to get into rentals to supplement my income and possibly retire at 60 (any earlier would be icing on the cake).Is anybody else in a similar situation?

Eventually building a second source of income for myself semi passively to supplement my current job.  

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