I would recommend staying on the lower in when it comes to rental income expectations. 

Choose cities in safe and economically diversified areas with above-average income and population growth.

*However, I'll ask that the rental income will be mine after 9/20, instead of when we actually close.

Issues like....How is the income split.Who's name goes on the property.Who pays for taxes, insurance, maintenance.

How long must I rent my Chicago condo out before I can count the income toward another mortgage in Florida?  

What are the real tax benefits to the seller when transacting via purchase money mortgage...I can see if the property is not a primary being taxed at capital gains for the sale...but what happens when the seller files taxes at the end of the year...how do they report income from holding a mortgage?...

I am hoping to establish my passive income through rental properties in the next 3-6 months.

If your numbers are accurate and you have 20% to put down, you shouldn't have any problem getting a conventional loan UNLESS you don't have another reasonable source of income.

I am upper 30s and looking at this for additional income and possibly a career change.

I know I will have to pay incomes taxes as apart of this conversion, but I've been doing some reading and can't seem to understand if I will also be hit with additional taxes as a result of something called "pro-rata rule".