I'm not so sure about that. Who's going to buy HLO that doesn't already own Classic? The new features are not groundbreaking enough that people who were on the fence about Hero Lab are going to be convinced to buy it now. Nobody is comfortable with the risk of spotty internet and the chances of ALL players at the table owning HLO to even make use of the features is low.
People that want Starfinder would have spent the same money for the classic version.
People who already own HL "might" convert to HLO but the cost (and profit) is minimal.
I don't think its a terrible idea, its probably not going to lose money, but I don't think its going to get new customers.
Edit: and if I was a RW customer I'd be pretty upset. Finishing RW would get me to buy in and they'd get more money from me for that than converting to HLO.
The proof will be in the pudding. When it is first released, I probably won't buy in as I'm only running and playing 5e and the new Paranoia (plus the occasional one-shot of highly obscure games that would not benefit from HL). But if they can offer the ability to have all my players' character sheets sync'd up with the tactical console on my tablet laptop and if they improved the tactical console to automate more of the condition tracking, and if it worked with the SRD, I would be all over that. I would buy for myself and my players and pay for the subscription. And that is after already plunking down a lot of money for DnD Beyond.
As for what I've spent on HL Classic, I don't mind the sunk cost if the new product is superior. It is easy for me to say that because, unlike many Pathfinder players/DMs here, I have not spent *that* much on HLC. That said, HLC will continue to be supported for some time and your content that you buy/bought for HLC will (eventually) be on HLO.
Of course, a lot of this isn't going to be ready at launch. I expect their focus is to take advantage of the popularity of Starfinder. If they offer a compelling platform for Starfinder, that should bring in a lot of new customers and convince many current customers to buy, which will fund further development.
As for upsetting RW customers, it is only really upsetting the KS backers. I bought RW for what it was and it serves me well. This is the risk with KS. If you don't have the appetite for scope and schedule changes, don't buy it until it is released and you can verify that it has the features you need.
I spend far too much money on KS. Most of my tabletop hobby spend is done through KS. I know the risk and I've been burned, but I get early access to some great products that may never see wide commercial release and often there are some amazing deals. I find it best to just ignore the comments, skim the updates when they come to my e-mail, and just wait for the backerkit or other fulfillment communication. If fulfillment never happens or the product isn't quite what I was hoping for? Ah well, a bad bet.