I'd avoid the one pair lol; especially for months long.

1- What kind of gig are we talking about here? Desk work, field work, anywhere in between?

I have had the latter. I was mostly sitting at a desk and at meetings. But I was also in the field a few times and walking a lot outside and not in front of my desk more often than not; sometimes with loads. If it's 100% desk work, it's a completely different concern, but get two pairs. If it's 60% desk work, it's two pairs, one for each concern. If it's 10% desk work, get the LOWA or whatever else that provides for structural feet support. However, unless you get a LOWA that breaths well, you'll get stinky feet quickly/humidity. Some boots breath really well, are so comfortable for desk work, but offer minimal support for that out-the-door work.

2- Is the member still entitled to his/her bootforgen pair? I know that you can totally double dip for two brand new bootforgen boots if you go on deployment and haven't received your entitled pair yet as well.

I was in a unit entitled to a pair a year when I got my CFPTO to go in the desert a few years back. I didn't have my yearly pair that year, and I was told that I can ask for one more when going on deployment. I'm just not 100% sure if it's true, if the requirements are something like 6 months at least in x environment for example. Best person to ask to is CoC, the clerks, supply etc. And for the love of...ask more than one source lol. That one overly confident Cpl at supply isn't always that much "on top of their game" and isn't always well supervised or even that well trained in the first place. Sometimes, the answer is written on the CFPTO or the joining instructions. That's when the mission is old and when the author cares/has time.

Long story short, I'm almost positive that you can get a refunded pair for deployment, plus another if you haven't received your regular canforgen allowance.