First, let's start by saying that making wort is very easy and forgiving. So take a deep breath and exhale slowly.
When setting up your equipment profile in BeerSmith, you want to get the amount of unrecoverable wort correct. You can easily do this by taking a measured amount of water and adding it to your herms system. It needs to be enough to recirculate to capture any losses that might come from the lines. Recirculate this until the flow is consistent then drain the mash tun as you would normally during your brew session. Measure the amount that you recover. The difference is the "mash tun deadspace".
You will want to make sure that your strike water volume will be enough to cover your grains. You can measure this by adding water to the mash tun and recirculating it until the water level reaches the bottom of your grain basket. Now, drain the water out and measure the volume. This volume is the "mash tun addition" in your equipment profile and accounts for water that is not in direct contact with the grains so that your water to grain ratio can be set to make sure all the grains have good contact with the water to enable conversion. If you are just using a false bottom, this step is not needed.
Next, You will want to make sure that you are accounting for the temperature of the grain only and not the equipment. You do this in the recipe on the mash tab where there is a small box just below the mash profile labeled "Adjust Temp for Equip" Make sure this box is unchecked. Since you will be recirculating the strike water to heat it, that will bring the equipment temperature up to the temperature of your strike water. The software will now adjust the water temperature based upon the weight and temperature of the grain only.
Now using this equipment profile in your recipe, BeerSmith will calculate your strike temperature to be fairly close. Don't worry about being exact, as you will be setting your controls down to your strike temperature once you add the grains and allowing the HERMS system to regulate your mash temperature. This is the 'mash in' step. There is a 'rise time' in the mash profile to account for mixing time and the time for the temperature to equilibrate in the mash tun. You can edit and set this time for whatever you want and I would suggest that you measure your addition and mixing time for the grains and update the profile with this value for future brewing sessions.
BeerSmith will calculate your sparge water based upon the remaining water needed to make the amount of wort you want. You have options on the temperature since your Herms system can easily bring the sparge water up to whatever temperature you want the grains to sparge at before you drain.
Slowly adding water to your mash tun while draining is kind of simulating a fly sparge. It is one way to doing it. I prefer to keep things simple by draining the first wort out (called first runnings), measuring the wort collected and then adding enough water in the sparge to make up the difference between my first runnings volume and my target pre-boil volume.
Mash out is bringing your grain bed temperature up to around 168F to 170F and is typically used to stop enzyme activity and to bring the viscosity of the wort down so that it drains much easier. You can do this with your HERMS just by increasing the temperature of the wort as it recirculates. When I use my mash tun (I normally do BIAB), I don't bother with the mash out step, as the kettle the wort is draining into is already being heated towards a boil. Then again, if I had a HERMS I might consider it.
The important thing is to feel out your system and make it work for you. There is no strict way of making wort and everyone has little changes that work for them. Once you have this down, the big goal will be to handle your process consistently so that you can produce wort in a predictable manner.
As I said at the start, making wort is relatively easy. There are so many ways of doing it and it is a very forgiving process.
Feel free to ask more questions!