I freelance, and most of these are not really pain points. About half my clients pay on Net 30 terms, so 7-10 days after the invoice is fine with me. Getting a check doesn't bother me either. It's an excuse to get out of the house and walk to the bank, so I actually I sort of prefer it over ACH. Re taxes: it's not that hard to be informed and do it yourself, but in the last year I've switched to an accountant and that's pretty nice too. I think he's saving me more than I'm paying him, even before considering the hours and hours (and mental energy) freed up from doing taxes myself. Re your last point: sure, who wouldn't want the sales process to be easier? But I'm pretty swamped with work as-is.

Here are the pain points I think about:

- How do I take a vacation? At any time I've got one (or two!) 20-hour/week projects, plus 2-3 extended relationships that require 5-20 hours/month. It's hard to spin them all down at once for 1-2 weeks. Seems like a partner would help, or even a relationship with another freelancer I could trust to be on call for emergencies while I'm away.

- Where do I go from here? I'm not sure how much further I can raise my rate for general-purpose web development. I could start doing patio11-style business value contracts instead, but I'm not sure I'm ready for that yet. I'd rather either (1) specialize in Postgres, Chef, Machine Learning, or whatever and double my rate that way, or (2) transition to an "agency" by seeking larger projects and partnering or subcontracting to get them done, or (3) get better at recurring revenue like support contracts.

I think ndcrandall has a nice idea. I could imagine a marketplace around helping freelancers trade clients, or even just help each other with overflow work.