I assume in the winter months they would perform well, but in the spring/summer/fall (non ski months) how do they perform? 

I would highly recommend you create a Market Report in PriceLabs to see how similar properties nearby are actually performing.

The math says to perform $500 sewer clearing each year instead of $5000 excavation, but the $5k bought peace of mind.

This is a task to handle carefully and at arms length. 

This would be a tedious task to do on a daily basis. 

Immediately, I performed a Roth conversion, and instead of paying taxes on $50K I'm paying taxes only on $21K.

Owners mistakenly ASSUME all PMCs offer the exact SAME SERVICES and PERFORM those services EXACTLY THE SAME WAY, so price is the only differentiator – so, they often select the first PMC they call or that calls them back!

@Christian Pichardo not a fan of Tom Cruz as he exaggerates everyting about his success to sucker people in:(Let's address several issues:1) Buying on recommendation of "Guru": what guarantees did they give you about performance?

I created the following decision tree diagram to illustrate the decision process (click to enlarge).The above decision process is based on the property’s performance record, with the goal of achieving financial freedom in mind.Financial freedom is not just replacing your current income.

Ironically its the investors in the layered LLC's who believe they are hidden in the cloaks of secrecy and better protected who end up in  the most costly and drawn out litigation while giving the plaintiff attorneys reason to take a more thorough look under the hood.Keep your LLC ownership simple, carry appropriate insurance, make sure ever vendor you work with carries appropriate insurance and those who perform work functions most likely to lead to liability exposure list you ad additional insured (not merely certificate holder) and it should go without saying, avoid negligent conduct.