You're essentially taking a 10-20% loss on day one. 

Also, to further protect yourself from large assessments, a condo owner can get what is called an HO6 or loss assessment coverage through their individual insurance carrier.  

We’ve all heard the terms fear of loss and fear of missing out.

I'll definitely get all of my investment and money spent on overhead back in the refi, but do I continue forward with the BRRRR, take the small loss each month, and bank on rates eventually coming down some more where I would refi again to bring the payment down OR pivot to flipping it where I'd make, easily, $40-50k net profit AFTER setting aside capital gain taxes?

The learning curve a killer but now I am stuck on unloading my burden selling it to break even or renting it out at loss. 

It won't make a difference, the total income / loss will be brought to page 1 of your 1040 or carried forward.

Consider consulting with an attorney and having them draft you a blanket feasibility contingency that covers everything you need to terminate in one contingency.

If she forfeits her last month's rent and deposit, that gives you through February to find a replacement Tenant before you start to incur a loss.

I'm able to take a significant number of passive losses on my rental properties. 

A house hack is like that beginner run (but BRRR'ing, wholesaling, and out-of-state investing are more like double black diamonds).The fact of the matter is: real estate is often a high-stakes endeavor, and the more advanced strategies (like BRRR'ing, wholesaling, flipping, out of state investing, etc.) can easily bankrupt a beginner when they're executed poorly.Plus, HH'ing is an ideal strategy while you're young...when you're in your 20s/early 30s, it's pretty common to live with housemates (or to live in a duplex next to your tenants), but this arrangement becomes much less feasible once you get further into your 30s/40s (especially if you start a family).Now, having said all that, house hacking is not necessarily easy (if it were, everyone would do it!)...