I am an investor in the city of Chicago and have house hacked multiple times.   

What if you have multiple bank accounts? 

If your area requires multiple ways of sending the letter, you do it all.I do not know if you'll need to go to court.

Which means I could have money to purchase multiple properties.If I keep it, I can rent it out for $1,600 a month.

as i keep reading through the bigger pockets book on rental investing, i keep running across these sections that say "this isn't expensive and shouldn't cost more than $1000". but I've read things like this multiple times throughout this book.

First month told permits are taking longer than expected but was told everything was ready before I purchased, following month told footers and underground plumbing was done.Through multiple emails every month being told the same progress footers and plumbing they forget what the tell methe previous month.

Would a bank really loan me money for let’s say 5-10 rentals while I only make $45,000k (debt free)
If so how does it work.

Thanks guys for the help.

The assembly version , has a yearly "fee" , a mandatory registry, inspection mandates, a water tax(for cape cod) and, most ominously, a graduated tax rate applied to owners of multiple properties.Like your area, Cape Cod ,has been a thriving short term rental market long before the internet was a thing.

Very engaging and inspiring as a new investor. 

Usually people just want to break even so they can use it for free multiple times per year.