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.

I went to Boulder city after the market fell and I saw condominiums that were listed for 150 000 that would generate rents of probably 12 to 1300 a month and those condominiums were selling for 50 000.

Your sanity and peace of mind will be more intact on that path and you'll also have more time available to keep on with certifications and eventually an MBA to boost your income even more.3)  Once the income stream ("just over broke" as Robert Kiyosaki calls a "job") is in place to generate much-needed capital, I would settle into a very frugal life to begin with. 

The new generation of Smartkey don't have the same flaws, but they are vulnerable just like any lock.

I am currently W2 employed but planning to retire early.

All of the units generate income, just not fast enough for the amount of issues we have had to manage.  

I plan on investing in a live-in duplex or triplex BRRRR while employed in the Canadian Armed Forces.