This includes monitoring the transaction, conveyancing, compensating my transaction coordinator, and dealing with both sides paperwork and timelines - not including negotiations. 

I would closely monitor your competitions pricing to see what is working for them.Vrbo has built in tools to monitor when people are searching for specific dates.

I recommend reading the book traction and following EOS - they have a one page business plan that is awesome to follow. any planner can work it's a matter of creating the plan and how to monitor and follow through with it which eos teaches

I think the 2 biggest hurdles are finding the right team to do the work, given you won't be there to monitor it 1st hand.

Be prepared to answer how you will monitor the property. not everyone asks and not everyone will press hard on this, but it's good to be prepared, especially for rehab properties.4.

who can monitor your investment closely.I hope this provides some perspective on the situation here in Italy!

Most are folks that have the emotional control of a 5 year old, controlling attitude, an omniscient narrative in every thread & topic, act like an online hall monitor, and constant attention seeking. 

Focus on the big moves: security, renovations, and cutting dead weight. 

Once you've identified what's important and what ratios to look for to evaluate a property, all future deals should be weighted against those "good" ratios/numbers - and periodically adjust to suit your goals.

The foundation was already approved, permitted and finaled years ago for a 3400 sf house, and its solid and I won't be building directly on the overhang edge; but rather back away from the edge a few feet to prevent any load issues all the weight will be on the longer sides of the existing footing.