If you do get in though this could generate a few hundred each month but keep in mind these rentals don't always rent and get occupied same day so a month of holding costs may eat up a large part of your profits. 

Some of my goals are: -Retire Early (30-35 years old)-Live very comfortably or better with the ability to travel when and to where I want-Have more time for friends and family -Build generational wealth for my future familyI know that this is a lot of information and can most likely have a post for each section I covered but I wanted you guys to get a little picture of my life, where I stand, and where I want to be/when I want to be there.

In SF bay Area you can be cash flow positive with 25% down, and after few years can easily generate 5-10% net profits. 

Last time I saw this I was in Greece in 2007, learning the flip game in an environment so out of whack that after the bottom fell out of the giant Ponzi scheme that the country had become, the Greeks were forced to admit the situation would take generations to fix.I'm not going to cry doom and gloom.

The refi step in BRRRR is to generate a cash position for the next purchase. 

Or does it need to be generating its own money despite the quantity?

With this being an income-generating property that is cash-flow positive, this should not have negative long-term effects on you or the co-signer's DTI. 

I feel at this point in my life I get more excitement out of buying the next property than I would get just putting it into our savings or spending it on random junk. 

A couple weeks ago I built up the courage to walk into and random real estate office and ask the broker if he was basically willing to teach me the industry. 

Aquire a vacation house to use like 5% of the time but still have it as an asset generating positive cash flow and not as a liability3.