I am attempting to work with a property manager but I'm seeing a read flag and would love some input.This company wants to charge a 1 month placement fee for a new tenant, which I am totally fine with but also is saying they would charge me that fee AGAIN when the tenant renews their lease the following year.

Won't do it just for more moneyGo to the Short-Term Rental forum and read up on rental arbitrage, or use the search feature (magnifying glass).

Has anyone had any experience with building silo homes?  

Consider hiring a property manager if you don’t have the time or experience to handle this.Maintenance and Repairs: With multiple units, maintenance requests may come in more frequently.

You can read the forum and create a list of the 30 most common problems, then study how to handle them and develop a plan for each in less than a year.

If so, what was your experience with the septic system inspection?

Also, I think a newer building would make my life as a landlord a lot easier since I don't have much experience and wouldn't have to worry as much about stuff breaking down all the time. 

Ideally, I would like to buy in the Catskills since it’s close by, a popular year round destination from the city and has a history of vacation rentals but I know there’s more and more talks of regulations so I am open to other areas and would love to hear your thoughts/experience on the area.Would love to connect with anyone who has interest in the area and the short term world as well as agents familiar with STR who could help us in our search.

I wouldn't buy one from scratch if you don't have the experience. especially in miami where it's one of the most expensive places for land in the country. the areas you are talking about can exceed more than 20 million an acre depending on height allowances  

All that aside I'd do it, especially the part about including your kid and exposing them to the experience and related tasks.