This covers a ton of ground for finding renters.

What I like is that they use 2 people to inspect so they are able to cover quite a bit of area very thoroughly. 

I'm a little leary to think that 6 nights (3 weeks * 2 nights) is going to be enough to cover mortgage, insurance, property tax, maintenance, cleaning, furnishing, 100% of utilities, cable, internet, etc. but maybe I'm all wrong. 

I want whatever cash flow there is to cover the expenses in the long run...I could sell it and take home some cash but I don't need the money now.

I have my utility lines covered on a policy written by Philadelphia Contributionship.I have a couple houses that I've been too lazy to switch still with Nationwide (I think) and they DO NOT provide it.

If it is near the city, meaning more of a rural area, turnover will cost more than what’s covered by a 10% vacancy projection, just because of the lower demand and smaller pool of potential applicants.This is a very unattractive “deal.”

Your friend has about $7k per year cost of maintaining her property - if we ignore utilities (unless they are included in the condo fee, which sounds too low to cover all utilities) and maintenance. $280k divided by $7k is 40 years.

Lucas started down this road, but I think the most important part here is to very rigorously vet the would-be tenant and get enough written assurances that you are covered if this doesn't go well. 

Alternately you could send them all a notice explaining the situation and indicating that if there is another fine that you are simply increasing all rents to cover the potential costs. 

You need to plan for vacancies and figure out who would cover repairs.