. - The insurance industry like many others (including our industry of home remodeling here in Chicago) has escalated exponentially in cost.I've got several local Chicago brokers I can share with you, but I think no matter what your rates & premiums have probably gone up...I will send over a couple of contacts for you.Just curious, what neighborhood of Chicago is your building in?

So any help means more than you will ever know. 

If the cosigner/guarantor owns real estate for example, any unpaid judgement will become a lien on that property and raise the odds significantly for eventually getting paid.If the cosigner/guarantor doesn't have assets like real estate to go after all they are offering you is a promise and last I checked you can't cash a promise!

(they do charge a flat $2 for ACH, but tenants will pay that).

What tips do you have to determine if a property will reasonable rent quickly in a given area at market rents?

A 5 year life span component will have a higher deduction is year 2 than year 5.

The Holding company will be the "Member/Owner" of the 3 LLCs (2 property holding LLCs, and the new Property Management Company LLC).The purpose for this then would be that I would really only need to manage "books" on the property Management LLC, and because the Holding company was the owner of all 3 of these LLCs, I could use the property Management LLC to pay all of the bills, collect the rent, maintenance etc. 

Keep in mind, though, it will require significantly more time and effort but offers the potential for higher rewards through forced appreciation.If you aren't wanting to be as hands on with your real estate and want to approach it more as a side hustle while you focus on your career, the turn key option may be better.

That will give you an accurate, real world number.

Any guidance on this will be much appreciated.