I did go sky diving a few months ago and have a snowboard trip planned for the winter.

One of our properties had a proposed increase of 3-4x.Water & Sewer shouldn't be a huge concern, but you need to go a layer deeper. 

We basically just don't want to dive into it without all ducks in a row and we can't make any moves until we have this part figured out.   

I think you have an amazing opportunity and that it's a good time to dive into investing in the market!

It seems like your friend is only sharing the profits (if any) but is not sharing expenses, risk or potential losses.It could be a lending relationship more than a partnership, and frankly it would be better if it is lending.Needs a deeper analysis, in my opinion.Either way, it is NOT income to you.

Without know ANYTHING about your HOA coverages, or your renters insurance policy, I would say that it sounds like you need to dive into your policy documents.Most (not all, but most) HOAs cover "Walls Out", meaning that the exterior of the unit. 

What are some quick tips or hacks for recognizing a good deal before digging deeper?

The issue with the second one is if it doesn't work as planned then he just digs himself into a deeper hole.

I am not saying I am jumping the gun and diving in.

As you dive deeper she states that the largest “cohort” of millennials turns 29 this year and 30 in 2020.