It was a bit more complicated for the taxes but your local CPA should be able to handle it.  

For a residential, that gets depreciated over 27.5 years as per IRS, so if you divide by 27.5 you'll get your annual depreciation =  $5,454, let's round it up to 5,5K[Again, this is simplified as things get more complicated in the first year when depreciation is prorated and get even more complex if you accelerate depreciation with a cost segregation].So, now if you have positive cash flow of, let's say 10K, you''ll have to subtract the depreciation and end up with a taxable rental income of 4,5K. 

A secured note is not a complicated process.

If there are complications, then the sky is the limit. 

He's a former business partner and has handled some really complicated deals for me.  

It seems more complicated than the suburbs like Naperville.I am from Naperville, and is it a better idea of investing in Naperville even though a bit far to take care of the property if I buy in the area?

It's all very complicated and I would say ask you attorney, or an evictions specialist in your area, to be sure.

Is my mortgage broker not going to the extra mile or are our situation a complicated one ?

This has been a big, complicated tax mess we’ve had to deal with.

I've run into complication of violations and passing on the cost when the tenant is at fault.