You are new, so you don't have a pool of contractors, or know what things really cost, or what a scope of work truly entails and if you are getting fair bids or not.  

@Alfredo Cardenas Passive losses from rental properties are generally pooled together, not separated by property.

Do you get a decent rental pool?

The question I have is have any of you rented out a property with a pool and if so what safeguards should I have in place to protect my myself?

Possible coin machine needed nearby (although most are CC today), additional lighting for added security of both machine and customers.To your point, you do see vending machines in the 200+ unit range, often near or in clubhouse and pool areas.  

Just rented a fully updated pool home 2 bed 1.5 bath for $4,500 this last week so the pricing can definitely fluctuate.

Is a solar pool heating system a wise investment?

When I dove deeply into the social media pool, I had no idea I was going to capture a tidal wave of undiscovered real estate investing opportunities.

And make sure that all items necessary for you to get the best rate possible from your carrier (like 4 point inspections, roof attachment points, pool enclosures etc) are present or available.One nasty little factor that can't be helped is that every time you buy a property for more than than last owner paid - you will have a tax bump due to re-assessment. 

The tenant is in your property because he cannot afford a place with central air and a nice pool!