I looking to get a consensus of what is the top 3 biggest cost for rental properties owners occur on a consistent basis?

If that occurs at all it is usually in multi-family properties.Single family the tenant typically pays everything.

I’m guessing it’s one of those things that are bound to happen… Don’t mind organizing the events, but don’t care for the public speaking part.

In the event of a successful foreclosure action, the mechanic's lien will be wiped out by the foreclosure.

The holding agreement should state that the holding fee will be used for security deposit and first month's rent upon signing of the lease or forfeit (at least 50%) if they back out. ...The only problem with a holding agreement occurs when you want to have the tenants get the utilities into their name before the move in and the utility companies require a signed lease before they will put the service in the tenant's name. 

Having said that, I still prefer the standard contract as it conforms to state law, and is designed to be fair to both parties, and covers a lot of the "what ifs" that can occur.  

Couple of tickets to a temperance event (pre prohibition).

@Renardon Calhoun I help run a event on the North Side of Chicago, which is nowhere close to you.  

In any event, the answers would certainly allow this analysis 'exercise' to pay dividends. 

Key Milestones (i.e. permits, materials being delivered, etc.) should be highlighted, so you remember to keep an eye on anything that would prevent them from occurring on time.)