Hey Andrew, take my opinion with a grain of salt as I am also a new real estate investor, but the roof shouldn't discourage you from buying this property.

That’s just my thoughts on this so take it with a grain of salt but in my opinion “where there’s a will there’s a way” and it sounds like you want the property.

Including cleaning the house, patching walls, peeled paint due to stickers on the walls, they left the kitchen really dirty, food in the fridge, etc.

<—— Love it Here are my brief thoughts on your questions, with the caveat that I invest in SFR and not multi-family so take it with a grain of salt.2.1 - No list is truly exhaustive as you’ll always run into niche issues, however I think this is a good start.

@Brad Klock  I am a buy and hold residual income all the way guy, so take my advice with that grain of salt.i would rent that all day, unless you have reason to believe the market has peaked and the neighborhood will soon be declining. 

Anybody have any experience with food cart pods or know someone who does?

Food for thought

. - 1 hour drive to another part of the island.If you're from Big Island though, you can take my suggestions with a grain of salt as you probably know more than me but hopefully this helps a little. 

I’m not even talking about,  ‘there’s a roach in my food’, maybe more of a ‘things could have been better post investment or my property manager sucked, or I can’t believe the premium I paid’.

So take everything he says with a grain of salt.