Just hard work combined with diligent saving and time.

Combine this with a mortgage and it's near impossible to get ahead.

This being NJ I don't really have a lot of leverage over the tenants either other than threatening them with a 10% rent hike, no NJ judge would allow eviction over stupid crap like this, or even unpaid penalties I might impose.Do I just suck it up?

Hawaii's population is very debt adverse so people are very fiscally conservative... that combined with the fact that the ohana comes in and helps if anyone falls behind.... means little to no foreclosures.In addition wholeselling is extra tough because Hawaii just has so much dumb money and international money chasing non cashflow deals that don't make sense.

In my view,The tenants should be the ones buying me the booze for putting up with their crap 

What if a combination of these issues happen all at once? 

Amazon and Alliance Bernstein were the biggest announcements of new firms coming to town and are supposed to bring a combined 6,000 new jobs to the area with an average pay of $100k or more - as it stands, those jobs have yet to arrive.

The 3-Family and the Single Family now comp separately rather than combined against a 4-unit house in a worse location with smaller lot size (as had always been the case).Added roughly 250k+ in combined market value.Lessons learned?

This deal is due to combination of luck, timing, negotiations, etc. to get to current shape.  

A blanket loan will not lower your dti because the loan amount would be the combination of all 4 properties, which is the same as them being separate.