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.  

You are buying into the property, the renovation that was done, and the management, and sometimes the tenant.Rent-ready is a renovated home where you do inspections, close, and find your own tenants using either an agent or a property management team you find.

If you decide to sell anyway and buy a new rental you have to invest all cash or you’ll be taxed, so you have to put the $1.95M as a downpayment. 

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. 

I am considering a 1031 Exchange when we decide to "move up" in home in the future.

I have a local property manager that is co-host on the AirBnb listing that will continue to manage the property.

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. 

I have a STR property that is in a FL land trust and I set up an LLC to property manage this property (collect rents, etc).