They tried to save money by filing themselves but ran into procedural issues that ultimately delayed the process by weeks.

It does not take any revenues from them, it is revenue producing for them. 

It's not as simple as simple as buy now and hope that "time in the market" will produce a win for you.

Stats can be foundhttps://www.ramaui.com/housing-statisticsOr for all islands herehttps://www.hawaiirealtors.com/resources/housing-trends-2/Your realtor can produce more specific stats on your area of interest.

You can go as low as 2.5x in some cases but NJ tends to produce enough traffic/applicants where 3x should be minimum unless property is over priced.

Cheap money and low rates produce euphoria, which increases flow of money to an asset, which pushes up the price to uninvestable levels.I think it's going to get worse than better in the short term.Gino

When you go to sell the property, if you produce a certificate of inspection for the wrong number of units, buyer unless you are giving them a great deal and they will throw caution into the wind, would insist on the correct designations.

It may not get the number of wind/hail storms like TX does, but when the storms do hit in MN, they're usually very large systems, and produce awful hail damage. 

The rent plus his retirement will actually produce positive cash flow.

Find the best property you can afford that also can produce enough income so that your monthly out of pocket expense is equal to or less than what you'd pay in rent.