I'm walking with a contractor today to get a rehab ballpark estimate before making a formal offer, but want to be prepared for the next step should my offer be accepted. 

This can help you find deals that aren’t listed publicly.Work with Real Estate Agents: Find agents who specialize in investment properties.

So again, I think that comes down to, are you all prepared to make that balloon payment, can you hold on and get to where you have "passive" income coming in from the STR, or do you want to get in and out quickly to make a good chunk of change. 

I’ve done rehabs on the mainland, and this would be my first in Hawaii so I want to be as prepared as possible and ensure my analysis accounts for everything (or as close to!).

Going through the U&O process right now, it was helpful to get a copy of the previous inspection to better understand what they look for to be as prepared as possible

I converted a few apartments to that purpose, and listed them with a company specializing in that field, however they have not found a tenant yet, and I've listed with them for 2+ months.Would you be able to share which company you are using?

Nevertheless, most never appreciate the nuances of negligence vs. gross negligence for these reasons but the small fish who get caught up dealing with gross negligence matters get bit hard and are rarely prepared.

Then possibly get hit with a $100k special assessment while you have it?

Good morning,Can anyone recommend a reputable general contractor who can specialize in rehabbing a multi family in the chicago land area.

If you go into multiple units eventually it may be the easy button to do that.We use Bizcor which specializes in STR sites, but it may be overkill again as I think they cater to PM's.