There were no issues while you had a good tenant - which left on good terms and stayed for 2 years (Much longer than the average length of tenancy for Toledo standards)Bad tenants do occasionally happen and unfortunately no matter how hard you pre-screen them and how far you dig into a person’s background - you can’t always avoid the inevitable . 

Dora is about 45 mins from Disney and other attractions, so its in the ballpark for your 'standard Florida' tourist who thinks outside the box on where to stay. 

Just work it into the deal ask them to file the claim, maybe even offer to cover the deductible for a lower price. 

@Tim Krouse I’ve seen wholesalers have one contract supersede another or as an addendum to the standard contract.

I would be VERY surprised if there was any difference between how you treat a Month to month (TW) and a standard lease.   

What's the standard for paying off the cosigner.. flat fee, a% off the earnings.

Thank you in advance for any help!

@Joseph PuglieseIf your business is accrual basis and previously accrued the revenue and included it in taxable income, yes you could write off the bad debts.If cash basis, you don't get to write off revenue you never received as you never were taxed on it in the first place.There are extremely limited exceptions to this, particularly if you're cash basis and recognized the revenue under constructive receipt, however I suspect your fact pattern is not that complicated.You can deduct your normal operating expenses of the rental.Your CPA is best equipped to help you deal with this.

If it needs repairs you have to deduct that from the price and add that to your downpayment.

The 8 SFH is a standard mortgage.