I guess sports tournaments or other festivals/events/weddings.   

Part of the reason coastal values haven't quite scaled to heights of neighboring states is the remoteness and lack of winter sports and high end amenities and entertainment, but that doesn't mean trophy estates, ranches and homes don't exist.

hopefully something that can be set up online!

Your goal is to get a tenant who can navigate an online portal for maintenance request and paying rent online.   

I'm not sure why you are so bothered by someone sharing their experience online. 

There are also online platforms that will handle managing security deposit compliance, refunds, etc. like rentable.com

Quote from @Bradley Buxton: @Ryan KinoshitaI've used bluevine and there are some downsides to a online only bank.

Hey Peter, After working with several PMs I decided to manage myself using the online tools.

This is my personal opinion, which probably won't be popular.If you are worried about the cost of hiring an attorney to create a proper operating agreement for your LLC, you probably don't need an LLC, and if you choose to use an online site to create an LLC, you probably get the protection you paid for.

I could have just done this online.2.