I’m sure this has been asked before, so please indulge me if you will.
The topic comes up.

There is a pretty good post on setting up equipment profiles here:
http://www.beersmith.com/forum/index.php/topic,8579.0.htmlWort loss and Brewhouse efficiency are two areas I have no data on, as I’ve not made a batch yet to establish a baseline. What I’ve done in the last week is run a hot/wet test just to see how well the HLT comes up to temp with a given volume, and also checked to see how well/long it takes to bring the boil kettle up to a decent boil....
That's a water batch. Very cool to start with that because it helps set a lot of standards. You could get any lost wort numbers from transferring between vessels and fermenters. Just fill them enough to start a transfer and measure where it stops.
Brewhouse Efficiency is a concept that can take some time to fully utilize. Brewhouse Efficiency is the percentage of all sugars that make it to the fermenter. In other words, it deducts for all losses along the way. Most brewers use only mash efficiency, which is how much sugar from the grain makes it to the kettle.
Your question about getting 2 5.5 gallon fermenters out of each batch is a perfect illustration of why Brewhouse Efficiency is a better measure for the brewer to write recipes from.
Mash Efficiency: The sum of conversion efficiency and sparge efficiency into the kettle.
If you say you get 80% mash efficiency, you're saying of the total potential sugar available, you'll extract that much into the kettle. Pretty simple and straightforward, but it guarantees neither the expected gravity nor the volume in the fermenter the recipe calls for. This is because losses after the kettle accumulate to either lessen the volume to keep gravity, or to dilute gravity to attain volume.
The obvious fix is to account for the losses. Brewhouse efficiency expresses the losses as a percentage of Mash Efficiency.
Brewhouse Efficiency: The percentage of total sugar that makes it into the fermenter.
If you say you'll get 80% Brewhouse Rfficiency, you're saying; of the total sugar available, even with losses, that's how much gets to the fermenter. That means that if you add losses to trub, you still have 80% going to the fermenter and will maintain the same gravity.
Therefore, the ONLY place you can gain that sugar is with increased Mash Efficiency. Or, you have to reduce Brewhouse Efficiency by just about the percentage of volume loss.
There will usually be a variation in efficiency based on several factors, like grain weight, quality of crush and even particular types of malt. At the end of each brewing session, you can store the information in the brewing log and see the resulting measured Brewhouse Efficiency in the Fermentation tab. Over time, you can create an average equipment profile, or several more detailed profiles. I have a basic profile, then one for high gravity and another for high hopping rates.
A second question is regarding the mash tun weight. Currently I’m going to use a Rubbermaid 10 gallon cooler, so is there a known value for this that I should use?
The easiest thing is to just weigh it without the lid, on the bathroom scale.