Well done guys. Moving fast, being transparent and speedily responsive with founders (on investment and rejections) and keeping things simple have been central guiding principles for me as well, from the outset.
Not to pardon the lawyers but I think the main reason that DD checklists have become so (unnecessarily) extensive is that they evolve and get passed down from deal to deal. A lawyer, whose job is to be the “backstop” on risks, has a great disincentive to delete items from an inherited checklist — so they just accrue/compound/evolve from deal to deal, adding checklist items rather than eliminating. What lawyer would remove a potential risk-spotting checklist item that another lawyer used in a another deal — “what would happen if that item ended up being something that surfaces, and I saw it in another deal checklist and didn’t include it in mine?” he/she may ask. So the lawyers keep sticking them in, and have the “excuse”/rationale that they’ve seen them elsewhere (as noted above, often in much larger/different types of deals) — it takes very enlightened clients/investors to instruct the lawyers that, hey, it’s OK, let’s not bother the investee and ask for all that crap. The instruction to simplify the DD checklist has to come from the investor to their own counsel, because the lawyers’c ore inclination is to (perhaps overly) lean towards protecting the client (and themselves).