A good agent understands leverage and you want that working in your favor. 

When we acquire a new property with inherited tenants, who are more than likely a bit "old-fashioned", we usually give them some time to freely ask questions and don't change much at the beginning.

Just like airbnb where there's a trust factor, these workaway sites work in a similar fashion, but I'd make sure people have travelers insurance before arriving.Again, it's about the experience for both sites, and there were many hours spent playing board games, hiking, and ensuring it wasn't just a labor transaction, but a friendship that'll last too. 

When would you say would be the best time to start that, right after the house inspection comes back favorably? 

Do yourself a favor, take anyone's vacant data unless its directly from the city or the county.

I plan to research both options, but I was wondering what your initial reaction might be to this question.As I understand it, SBa loans would require 10% down payment and are generally favorable loans. 

With chicago having laws that favor the tenants already you lose even more leverage with tenants when you bring the illegal unit piece into. 

I was told that, I should prepare a letter in support of my project and send it to the city office and also speak about it during the public hearing.This is something new for me and I am looking to get some pointers as to what should I highlight in my letter and speech in favor of my project. 

Most of our coastal states are increasing regulations and creating laws that favor tenants, even when the tenant is clearly violating the terms of their lease on purpose.

I favoring taking out more HELOC than cashout the refi.