And he is setting up multiple future generations of needy people for help, which is even more selfless than "helping" familyMy parents will most likely die with some kind of modest estate and I could care less if I inherit a single dime. 

Having Multiple offers to give to the appraiser to justify the selling price also helps with what I’m getting.

And the heck with the one or two inquiries as the benefit of doing this a few months in advance can be extremely beneficial for multiple reasons! 

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.

From my experience on 5+ units lenders are going to want more skin in the game and I see minimum 20-30% needed down.  

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.