Not for the Dash address, no. The only downside of that if blockchain scrapers can follow the trail back to everyone they've done business with... that didn't use PrivateSend. Private keys... nonono!
Not unless they'd rather avoid promoting their business and would prefer not to have it mentioned on the interwebz.
I'd mentioned that one because quite a few folks I know personally are interested in those kind of things but as far as your proposals go anything that gives you personal legitimacy would be a bonus, some anonymous dude on the internet saying "gimmi loads a money and I'll do stuff.. maybe" hasn't much chance of getting votes.
Voted "yes" here btw, you've given a lot of references that suggest you're not trying to hide who you are, the projects you've been involved with are in some fields that I think would be really good for Dash adoption at the grass root level, it could couple up nicely with the Point of Sale proposal and there's a surplus in the budget at the mo and this seems like something that could make good use of it. Some might see it as a high risk for the potential reward and maybe that it has other risks beyond simply not providing value but it's worth taking a chance on imho.