Utility = Size of problem solved * Users
Do you have a good plan for how to get users other than counting on TC and virality?
If a product or service solves a small problem, what would make users transition from what they're currently using to solve that problem to this new product? There has to be some sort of incentive because inherently, we're all lazy and don't want to go through the entire process of switching existing systems.
Honestly, a simple group messaging app (or even email) + using Billmonk solves most/all of these problems. That's what my three roommates and I are using and there haven't been any complaints. As well, the more roommates, the bigger the need has to be in order to convince everyone to use this new system. The smaller the number of roommates, the even less necessary it is to have a new platform to manage all these affairs.
I think this is a cool weekend project, but would I call this a startup? I don't think so (at least, not by the definition Eric Ries uses in The Lean Startup).
Utility = Users * Size of Problem, just as Revenue = Volume * Price
Except that utility isn't always measured in pure revenue, as you can have ulterior revenue streams (advertising, selling data, etc.).
Whether or not users make the transition from the status quo to the new product is independent of size of the problem. It's different in each specific case.
I wasn't making a statement as to whether or not this was a good idea or can qualify as a "startup". I was reiterating the true statement that solving small problem for millions can be equivalent in value to solving one single large problem.
Dealing with roommates is no doubt a venerable problem to solve, but is there really a 'market' here that people will pay to address? There are so many lucrative and important issues out there, solving roommate management seems way down the list in terms of building a viable business. I base that last bit on the fact the OP describes this as a "startup" not a project.
I would emplor the OP to get out into the world more and find better problems to solve.
* = I use the term "debbie downer" after the recent HN post about searching for the weird terms people use in their comments. Debbie Downer was one of them.