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. 

I graduated from college with a business degree that had emphasis in real estate and i got a broker license in 1980.  

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. 

Graduated college last week with a degree in Christian Ministries (Biblical studies emphasis). 

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