Tanks

I don't want to be over-leveraged so my hope is that by having 3 properties support one mortgage I should be okay if the economy tanks.

It rides like a tank and drinks gas like its water.

We'd lose about 3-4 weeks of on-market time if this tanks.

One thing I haven't seen mentioned: UST's (Underground storage tanks) that typically store heating oil.

Back in 2008, before market meltdown, countless of investors acquired multiple properties (4 or more) in Florida at inflated prices only to be stuck with those same properties once the economy tanked and lending regulations changed.Like you pointed out in your original post, the key to acquisition and flip is location, location, location.

With the commercial units, even if the market tanks and values ascribed to them drops relative to their income, you can still build a lot of value RELATIVE to the rest of the market.

Each lot has its own septic tanks.

My biggest concern is that investing in my nesting grounds might not be the best place to start for the obvious reason...super high prices and honestly I remember after the 1994 earthquake how this market tanked.

It will leave you with a lot more options in life if you ever want to change it up and teaches you a lot about business if that's your major.Even on the Shark Tank, Mark Cuban wouldn't fund any of the brilliant entrepeneurs who said they would drop out of school if they got a deal - he felt they would be much better off finishing school AND working on their own business.