I know it could rent and essentially pay for itself.

Understanding the nuances involved in each investment decision deeply and weighing these factors according to your investment goals and risk tolerance is essential.

Essentially the developer / property manager didn’t pay our contractual rental income for years (a sum of nearly $30k) and I didn’t have much recourse.

I agree that it is essential to understand the differences in every sub-market. 

Below are a few things I look for in a vacation rental cleaner:1) Hot Tub Maintenance: Since many of my properties include hot tubs, it's essential that my cleaners are experienced in testing water quality and adding the appropriate chemicals as needed. 2) Clear Communication: Real-time communication is crucial for me.

Reality is you need to have knowledge of real estate principles, real estate law and real estate finance to be a successful real estate investor.   

On paper, they are essentially the same with some minor differences in offerings. 

There is a reason Wall Street investors buy single-family homes. 3 single family homes in the same area is essentially the same as a tri-plex. 

@Brandon CraigMissouri and essentially 100% returns since they are charging 10% fees and 86% return split so investors get 43%Clearly this is not an experienced investor sponsoring the deal as an experienced investor would show a 15-20% return and if returns were higher lower expectations which lower risk and if they got more they look like heroes.

In a healthy Association, they've taken into account that this will need to be replaced, and have planned for it, essentially charging everyone who has lived there over the last 20 years a nominal amount to be put toward the new roof when it's needed.With an unhealthy Association, they try to keep HOA dues artificially low, and when a repair is needed, they levy a Special Assessment, which puts the financial responsibility on those who live there currently.