My last eviction taught me its easier to work with a problem tenant getting them out versus forcing them out with their feet dragging.

(I ended up getting my real estate license last year as a side hustle too) because I was dead set on flipping/building homes.

No amount of insurance covers the personal loss.2.

1) I think it’s “funny” that not one news article I ever read for the last 5 years had headlines like “Housing at historical record lows!

Most people are happy just to not take a loss each month. 

.), how litigious is your state, your own loss history/ratio as an individual investor, the carrier's overall loss ratio in a certain state/area, the deductibles you've elected, etc. 

If I was to trade a $300k house for a $310k house that will cost me $10k and $347/month what amount should I ask for to make up for these losses?

- Do you think it’s worth challenging the appraisal with Kiavi, or should I just cut my losses and move on?

If the didn't do that then they have converted to LTR or MTR rentals at a steady monthly income and have the tenants take over the utilities which offsets the loss of more income.

There will likely be a partnership return required where you flipped a house with a partner and lost $120,000.If you sold the other property within the same partnership, it will also be reported on that partnership return.The net result to you is that you will receive a K-1 showing your income / loss which you then use to report on your individual return.If you made no money within the same year, you likely pay no additional taxes / get no additional refund.Best of luck.