When my handyman came to the property, I would give him the list and a credit card, and he would spend the afternoon driving back and forth to Home Depot.

For example, they'd pull 4 of 5 payments for a borrower from the same account and then blamed the borrower for not checking to make sure the payment was pulled before a late fee was assessed.

Background:  Late 30s, married with two young kids (4 and 2). 

Distance makes investing more challenging, as does seasonal occupancy and governments which operate differently and/or are less stable than our own(though our own government has not been a paragon of stability lately.)By investing in the Caribbean, you’re adding those challenges plus you’re throwing in the occasional hurricane.  

@Matthew Welk Happy to make an intro to the answering service team at CS Outsource that does our late-night support.They help with 24/7 emergency support, overnight coverage, troubleshooting issues, dispatching approved vendors & local staff, tracking and managing maintenance work orders, and other back-office tasks.

Good Afternoon, We might have found a deal, but we are debating whether the Rehab might be too much.

From there, it's already too late for the urgent stuff, and you'll need to chalk that up to a hard lesson learned about due diligence up front; trying to sell a property with urgent deferred maintenance is most likely going to punish you. 

To help keep it 5.0 I would consider offering, as often as you can, late checkout, and just a day or two before checkout.

Booking.com is definitely gaining some market share as of late.

Common fees will include a set-up fee, a leasing fee for each turnover or a lease renewal fee, marking up maintenance, retaining late fees, and more.