B2C startups have bigger caps because the network externalities allow for bigger bubble valuations (1MM users who never pay for anything, because the internet is free = $1B valuation). As PG has said- the value of such a firm is basically the chance they're the next google; therefore, no need to be profitable.
B2B businesses are much more defined, much more down-to-earth, and make good money. Whilst it won't be as sexy, it will make you money- possibly even without ever needing an investor.
Honestly, if you want my opinion- tell him you'll give him the files, and take your $150. Then walk away and never speak to him again.
Benefits: you free up time, you get him off your back, and if he wants to take you to small claim court for $150, he can (but he won't). It's just not worth it.
I don't think it'll motivate people to start up a company any more than "the replacements" motivated people to be pro footballers. I think it might get people thinking about ideas, but in the end, it's the execution that counts.
Whilst it's always great for society in general to have as many innovators as possible, I think movies like this tout the "sexy" idea, instead of the grind-it-out reality. As soon as people who were inspired by a movie notice that fact, they jump ship as quickly as the hopped on.
I think in this particular case, the devil is in the details. But, if we address your question in it's current black/white form...
Start by figuring out how long it's going to take to go cash flow positive. Double that time. If that doesn't leave time to do the rewrite, skip it. Instead, temp or hire a new guy who can back up your bottle-necked development.
I echo the sentiment of many folks on here- you pay for quality. As a development consultant and programmer, I've heard one too many horror stories from non-technical folks who just hired the cheapest freelancer they could find. That being said, freelancers range from $30/hr (for asian low cost providers) to $150+/hr (experienced guys in the USA).
If you're looking to build fairly robust web app that you plan on scaling, I suggest either:
1) Recruiting a technical co-founder and letting him choose a freelancer he's closely screened, and then micro-manage the hell out of the project;
2) Hiring a reputable firm to do it.
Either way, pay no less that $100/hr for good work.
B2B businesses are much more defined, much more down-to-earth, and make good money. Whilst it won't be as sexy, it will make you money- possibly even without ever needing an investor.