Thank you in advance for sharing your knowledge and helping bring a new perspective on land development to life!

Of course, try to get multiple perspectives from different loan officers before committing. 

Sell the house, clear the decks, get a job, start fresh.

Things have to go really bad from here, as I see it, for the office to underperform alternatives in the next few years, from a cash flow perspective. 

If you're comfortable taking on more effort for bigger rewards, BRRRR might be the way to go.From a tax perspective, BRRRR may be better because you can potentially benefit from accelerated depreciation on the property, which can help reduce your taxable income and give you a bigger tax advantage compared to a turnkey property.

Would love to hear others' perspectives. 

It’s great to see someone diving into real estate investing, especially with the unique perspective of being overseas in Japan.

This is my first purchase (don't want to do anything stupid) and the rents could swing 600/month depending on what I'm allowed to do in the basement - I'd be in the red from a cashflow perspective if I can't duplex them.Am I rolling the dice here / do you not typically find out for sure until you close and begin renovations?  

So I suggest really being clear about the "why" and the "what to expect" to keep these inevitabilities in perspective. 

The West End really could be revitalized and get fresh investment if it were breathed upon.