Claiming REPS is a red flag for auditors, so be sure you log everything in detail with your CPA from day one. 

From a financial perspective, loading up on insurance is more adventengeous than a LLC because if a claim arises, I'd rather file an insurance claim that give up the equity I built in a lawsuit.

Your profile mentions that you are a real estate agent - You want to have a conversation to see if you potentially are eligible to claim real estate professional status which would allow you to treat your rental losses as active instead of passive.Also have a conversation if you are required to make estimated tax payments since there is no withholding on your commissions.Lastly, your profile mentions you are in Florida which does not have a state income tax which opens you up to more options for choosing an accountant.

The roof and the floors were not huge costs to us the buyer, as the seller filed an insurance claim for water damage just prior to our offer closing.

I am looking at some  properties to purchase and was wondering if the amount of depreciation claimed changes if I bought the property in say the 3rd quarter of the year versus the 1st.  

If you were to partner with another more experienced investor to purchase a short term rental, do a cost segregation, and "materially participate" then you could gain the benefits you are looking for without negatively cash flowing, and you could work out a deal where you maybe only have to materially participate for the first year to claim your tax benefits and then you can act as a more passive investor.

:@Joe Splitrock turns out Cozy made an error and reported their failed payment, due to insufficient funds, to me as they had claimed fraud/disputed with their bank.

If a primary residence is converted to a long-term rental property, can bonus depreciation still be claimed in the first year?

Didn't you market a number of funds claiming they were "safe for retirement?"

Despite claims otherwise no money down deal are the rare exception.