As it relates to self-managing a large portfolio, I can assure anyone that if you have a great property from the beginning, no let's say you have 40 doors from Day 1 that are all properly renovated, you will not have more maintenance work in a year than one good full-time handyman can handle. 

I followed the advice from the insiders I'm connected with, which happened to corroborate my own judgement.Personally, I much prefer to stay in a short-term rental than an all-inclusive resort.

Sent you a PM / connect request. 

Take your time, take photos and videos of everything, and use the chance to connect with the seller or broker.

This will help you get a feel for the process without feeling overwhelmed.Network: Connect with other investors in the community.

I’m envisioning a platform with a rolodex of such professionals that get connected with tenant

Excited to learn and connect with you all!

Proper management and vetting of tenants can win people over but I think it's also human nature they'll never agree that it's better than what they thought should happen.  

As a real estate investor, I would like to learn how to properly put together a private syndication from an attorney with experience in this field.

I would connect with a closing attorney like Sperry & Hatley or 24 Hour Closing.