So, now almost two years later, I've had to close my flipping business because I can not seem to recover from this loss. 

REPS stands for Real Estate Professional Status—a tax designation that lets real estate investors write off rental losses (like depreciation and expenses) against other income, potentially saving a lot on taxes.

Flipping always seemed more risky and STR is riskier as well though it can be more profitable it can lead to serious losses. 

You may be able to get out of this bad deal with only your fees as a loss.

Put it on the scales, it's a loss.

Are you finding the deal, are you managing the deal (filling the units, taking care of the maintenance calls, making sure rent is collected), are you funding the deal or going 50/50 on profits and losses. 

Why we don’t like ARR (Average Rate of Return)It’s easy to skew the numbers.Here's an example of a positive ARR of 12.5%, but the investment loss is $50.Year 1 Start Value: $100 End Value: $25 Annual Return: -75%Year 2 Start Value: $25 End Value: $50 Annual Return: 100% ARR = 12.5%Am I missing something here?

If you don't have the vision to have MANY airbnbs in Champaign I'd suggest figuring out a strategy you have a long term big vision.Pros:  High cash flow (if done right), typically properties are oddly better-taken care of, sexyCons:  Management/system intensive, always on call, regulation can change things instantly  

Would depreciation on the equipment lower your taxable income, or do you already have tax losses to offset?

If the annual appreciation far outweighs the annual cash flow losses, it may be worth holding.