I know where you're coming from on the TurboTax Business stuff. Particularly when it comes to estates and trusts, moreso than corporations. There are tens of types of estates & trusts, and just as many ways each type can be set up. Combine that with the fact that state laws on estates and trusts vary widely among some states, and it comes down to knowing what you're doing.
Now TurboTax Business can handle many types of estates & trusts. But not all, and not all situations. The varying state laws tend to make the program rather complex since it can't be "tailored" to any one state or any one situation within a state.
One issue is that with a "living trust" (which is what I think you're dealing with) there are situations where if the trust was not set up correctly to begin with, when the owner of that trust dies, then the trust dies with them - meaning it's no longer a living trust. Then, that may or may not necessitate the formation of a "new" trust for the deceased with a completely new EIN and all assets of the deceased and the "new dead" trust being transferred into it. Then disposition of assets has to be dealt with from the new trust.
Now I've only heard of this particular situation one time in my adult life. That was on a "living trust" originally set up prior to 1985 or so and because of changes in the state law governing such trust, but the time the trust owner died in the 2000's, the only possible way to handle it correctly was for the "living trust" to die and everything be put in a new trust for disposition. Were it me in the position of trustee trying to deal with it, I'm sure to have screwed it up without professional help because I would have never figured out what I needed to do otherwise.
Now-a-days I living trust can be set up so that it can be used for final dispositions. But since the one you're dealing was established back in the 90's, I'd not be willing to risk it on my own.
