You can easily lose capital gain rates, plus there is the issue of refinancing.

To replace the roof I will be required to pay a $2000 deductible or I could repair the damaged area; which could cause me lose my roof coverage after 1 year, if not replace.  

I recently got a bid on a project from some non-flipper friendly contractors who basically gave me a bid that was enough to just build a new house with.Hopefully I can get some quick responses otherwise I could potentially lose the deal.

They will have little to lose and probably won't care about you or your property.

Let's not all lose our minds here. 

You may lose the benefits of property owned individually, like using building permits or representing yourself in court.See www.GeneralRealEstateAcademy.com for more info on TIC Agreements and fractional interests.

You’re better off just paying month to month so if you decide to cancel your services with them, at most you’ll lose money for only one month. 

Sitting in a bank account getting .05% is boring and essentially losing value.

Any buyer that you will be advertising to is going to do their own analysis of the property and if your numbers don't make sense you will lose credibility with that potential buyer right away.

Depends on how motivated they are too, if they worry about losing their buyer they might cave or they might just say no.