Hi @Josh Walker,Your lender local to Detroit must be using some homeowner's insurance premium "shouldn't come in higher than..." assumption(s) to qualify people because HOI is part of DTI.

Hawaii law requires an on-island manager, but in order to qualify as an active business I’ll need 100 hours managing the property so hiring a regional manager may hurt my tax write off plans.

If they 100% cant qualify without a co-signer and the co-signer doesn't qualify then they are out of luck. 

not sure about your experience but the second loan you got sounds like a great deal.most lenders really price by experience to get the really low rates very few will qualify for the best rates..Experience has more weight that fico in the HML world. 

Would you buy many SFH's or would you by a few 2-4 unit MFH's or would you go for the big one and use all $500k as a down payment towards the biggest MFH you could find that you qualified for? 

When the time comes, I'd like to meet with people who I think are qualified and experienced in this category of RE investing. 

It just depends on how the loan is structured, your FICO, and your experience/qualifying income. 

He had told me that I’m not qualify for primary residence due to me not living within the qualified distance.

You also have to qualify for Chp 7, you don't just get one.

I'd talk to a Qualified Intermediary before you make a plan.It looks like the government may pass 100% Bonus Depreciation.