In order to underwrite successfully you gotta' know the numbers and have experience.

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.

Has anyone had any experience with building silo homes?  

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. 

Anderson, a trusted individual, your corp/llc?

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.

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

While it may not provide immediate high cash flow, it could serve as a valuable learning experience and a foundation for future investments.Remember, successful real estate investing isn't about following a one-size-fits-all approach.

They typically have order taker LO's without a lot of experience and they have generally are not going to have much product that is outside the box at all.