You'll want to work with a savvy Tax attorney, business attorney, and CPA to make sure this is a valid tax avoidance or optimization play, and not a tax evasion play.In the end, Bellman, I will tell you what life has told me:  Occam's Razor is for real.

So far the CF looks better on Multi but if we play appreciation SFH is good. 

This will all play out over the next 2-4 years, not the next 2-4 months. 

[We played "Cash Flow" by Rich Dad Poor Dad and that game ROCKED my world with insight.

I've played with the rent vs buy calculators online and the result is so dependent on so many factors, so it's hard to know.

Then we reverse engineered that process as a starting point.And yes, those ugly P&L statements you see tell the story of PM's that play the system and play their landlords eventually putting them out of business.

And different variable play into the process as you move through it. 

I would recommend doing a house hack in Seattle for appreciation play and also invest in MKE for cashflow.

To answer your question yes market conditions in the past have played a huge role in the success of many deals.

I'm not an accountant and don't play one on TV.