Commenting on אעבדך שבע שנים ברחל (Gen. 29:18): אין ספק שלא היה הצדיק נושא אשה ומעמיד בנים אם לא היה בידו לפרנסם בפרט בשאר וכסותI'd agree with Gil that having a reasonable plan is probably enough, though it seems Yaakov didn't necessarily agree; otherwise he could have married her first and then worked for Lavan (unless Lavan would not have agreed to such a deal, which is certainly possible).
[Gil:] Let me translate into English: There is no doubt that this righteous man (Ya'akov) would not marry and have children if he did not have a way to support them, particularly with food and clothes.
Update: I should add that it's particularly worthwhile to note this when one considers the trouble at Beis Faiga (and other schools). Greg notes on Baltimore Jewish that it seems Beis Faiga was more prone to taking (exclusively?) students from families where the father learned rather than worked. [If someone can verify this it would be appreciated.] Certainly it is likely that many families were in such situations. If the school could not pay teachers because they had trouble raising and collecting tuition, that means the problems are directly stemming from clear issues with how the community works.
I was speaking to a Mashgiach earlier this week and was pleasantly surprised to see not only his sharp understanding of the financial mess, but what he had to say about schools. Noting a school that was heavily reliant on donations that is now facing massive cuts if not closure, he said that the school should have - while times were good - learned how to make themselves financially viable from within and not reliant on external revenue sources. The same applies to the entire Jewish community, whether on the individual, familial, or communal level. The more each person takes responsibility to doing so the more 'cushion' we create to help those who truly need it when problems arise, and to support those projects which we deem worthwhile to use our extra money on.