Historically, members had to file, manage, record, and report each LLC separately which meant more paperwork, more cataloging, more expense, and more reporting.

Being in CAN I find it easier to self manage and hire a team.

I primarily delt with non- performing 2nds, they prefer performing 1sts, so it's definitely a different animal,  but manageable. 

I will help run the STR, but I told him he needed to get property manager from the onset.

Because if not, now you are reliant on contractors and such, and there is a significant learning curve in this industry just around how to manage them and not get exploited or ripped off.  

We have property managers and don't run the small business, so my workload is minimal.Of course I keep an eye on the market, but finding anything for a guy like me would be way too much work. 

You may also want to call local property management companies to get their estimated rental amount and their feel for the rental appeal of your property in the area, etc.* Talk to your tax professional and find out what your tax implications are from inheriting the property to buying out your brother and putting it in an LLC, etc. * Also find out if the property's tax assessment changes with any of the scenarios above.

I think the actual settings will vary if you are managing directly on platform or using third party softwares, etc.As mentioned above I think risking going vacant over a major holiday will outweight the extra housekeeping cost.Also, I am not sure how much volume you are doing but do not pay cleaners extra for holidays. 

Since the properties are based in CA I will have to register the WY LLC in CA which will expose my ownership and thus I will have a member manager trust that will be the owner of the LLC.My question is who should I make the trustee of the land trusts?

With occupancy rates, utilities and bills the math works out that long term rentals are going to be more manageable.