However, one of the downsides is that if you're going to use a property manager, you have to use the on-site Property Management company in order for your guests to get access to the community amenities.

The biggest vacation rental house at the time was a massive 7 bedrooms.

@Maximillian Engram There are no downsides if you plan to actually focus on sales and invest.

The biggest missing piece here is your budget? 

Biggest animal request I have had. 

YES, we may be a little biased, but check out our blog here on BP comparing Detroit to other cities and Deep Dives on Metro Detroit cities & neighborhoods: https://www.biggerpockets.com/...Your biggest question shouldn't be WHERE to invest, but HOW you will invest!

@Corben BriggsProper has been the biggest name focused on STR insurance for awhile.

What are the downsides?

Down side I guess would be when you lose one you lose alot.

Your biggest risk if you execute the plan will be running out of money in retirement, either due to natural longevity and/or later health issues draining your resources.