I have no more qualification to speculate than most posters here, but here's my two cents, for what they're worth.
One wonders if that wasn't some of the reason why it's such a long lead time. I am sure DL would want their own branding up there. it kind of makes sense if that was the case, as like others, I have often wondered why it was announced that way. Although the expense for 1 flight a day would seem to be excessive, at least AA and B6 have 2 and 3 respectively, but of course having looked at the recent financials that Massport produced for ORH, they are so far underwater at this point, I am not sure the expense of Jetway 3 will really make much of a difference, they need to almost quadruple the number of flights, if not more, to generate the kinds of revenues needed to outweigh the cost. ORH is clearly a long game for Massport, because right now it's a money pit in terms of profitability, so they are going to need something spectacular to turn that around, IF they really want to do that.
Adding another jetway to the ready terminal pales in comparison to the money they spent on the Cat-III system. They could always ground-level board if they wanted to (either from the existing ground-level gates or another way) but I don't see that happening.
The plan for ORH, as I see it, is to get it to be a legitimate alternative to BOS for the central part of the state (as well as NE Connecticut and SE Vermont). The capacity increases at BOS means that peeling off some flights to ORH is part of a way to delay gate additions or other costs at BOS. While I'm sure Massport is always head-over-heels about current BOS revenue and the fact that it's more popular than ever, it's starting to become a victim of its own success in some ways. Every car you keep out of parking or driving eastbound on the Turnpike is probably a win for them. The kind of money you pour into this is a 20-30 year lead time kind of thing, as you know.
Also, having ORH as capable of taking RJ/A320/B737 sized diverts isn't something to ignore. With the Cat-III landing system in place, ORH is at least capable of playing defense in bad weather now versus shoving its hands up in the air. A B6 gate agent told me that a bunch of BOS-bound travelers wound up taking the ORH flight back during the bad weather the other day because, perversely, the WX was better there than at BOS.
My question is, IF they want to do that (and it's a big IF), what on earth could the strategy be and could they attract enough pax to warrant whatever strategy they come up with, given some of the other infrastructure concerns (signage and the like) that the airport has. Could they tempt UA to turn up with an EWR flight, how about AA or UA to ORD (although DTW will work for some of that with DL), or is this one open for a G4 type arrangement, but they might potentially overlap the B6 MCO service as an example. It's all conjecture at this point of course, and Massport isn't giving up anything relating to it's longer term strategy right now, or obviously what's going on behind closed doors.
If I'm an ORH planner, I would look at AA/UA/DL to hit the following destinations:
DCA/IAD (slots mean DCA probably won't happen, but it's the next logical AA destination in my book)
ORD (AA or UA, most likely UA)
CLT (AA Hub, tons of connections)
ATL (DL, very unlikely, but if we're talking hub flying...)
DFW (AA, extremely unlikely for a variety of factors)
I don't see a logical expansion plan for B6 based on their current destination list. B6 could try DCA, but again, slots. BWI is less appealing and they have no connections there. This is also not counting any left-field suggestions like F9 or NK.
They are being quick to announce the positives, trying to generate buzz about their local airport, but there has to be something else going on here, they wouldn't have invested over $35m in field infrastructure improvements (CAT III and the like) if they didn't feel they couldn't get some kind of return on it. If you assume a life of 25 years of the equipment and construction set up involved, that's about $1.4m a year + interest on the funding on revenues of only $2.2m before you add in operational expenses. Either Massport are experts at throwing money down the drain, which given their history, I am not sure that they are. Or there is something else long term here that we are yet to figure out.
They're playing the cards they have right now. The way I see the $35mm investment is that it was a do-or-die thing: if the Airport wants to be competitive for actual airline use, they have to have level of service where a random fog roll won't kill a flight, and the new system has improved minimums for non-Cat-III approaches which helps. The city had a choice to make in the mid-late aughts doldrums: demolish the terminal and revert back to a GA field, or sell off the land. The city made the choice for the former by selling to Massport.
I also see a division in Massport's money and airline's money. While Massport is doing incentives for ORH service, the cost of running the airport is a different time scale from airline's cost of service and profit margin. On your 25-30 year scale, the 1.5-2m/yr cost is peanuts compared to Logan's operating budget, for example. Worcester is also in a different place than it was 15 years ago: it's on the upswing, growing and shaking off the bad times. There's also the rest of Worcester county, which is almost a million people. For them, driving to ORH (even with the lack of direct freeway connection) will still be less painful than driving to BOS, BDL, or even PVD.
Speaking of poor access to ORH, I'm reminded of the decade+ that it took to get the bridge and highway over the Merrimack River to MHT. One culprit was a nesting pair of eagles along the river precisely where they wanted to build the bridge. The obvious irony not lost on anyone here was this: MHT had its heyday before the bridge came along, and collapsed once it was completed.
ORH doesn't have a river as a physical barrier, but its elevation does it no favors. I really think, on the north side, eliminating the roundabout at Newton Square and improving signage and guidance along Highland and Pleasant streets will help a lot in the interim. Building a direct airport road would cut through swathes of residential areas and I do not think would be worth it in the short term.