Being able to be an attractive employeer benefits wise to have & keep good workers.

I currently am employed full-time as a construction laborer in the area and at least for now have limited bills (car, rent, phone, groceries).

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

If it's your first time buy and hold property and your employment income is iffy they are probably only going to go 70% LTV (where the V is appraised value not purchase price). 

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. 

Yes, I was offered a couple of software programs for lead generation and tracking that were an up sale. 

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.