I have built a similar program for tuition collections at private K-12 schools. While quite successful, it took a large sales effort and big investment in IT - online access for both the primary (school/assoc) and secondary (parent/homeowner) customers, various payment method choices (ACH recurring, telephone, web initiated, credit card, coupon) loads of delinquency follow up (mail/e-mail/phone), etc. Schools also like to break down the payments into various fees - associations may need separate tracking for one-time capital assessments, etc. Profitability comes with scale, I can't see making much if you only have local associations participate. Success also breeds competition, so you need to stay ahead.
Compliance issues we needed to consider include GLB privacy, CIP, fair debt collection, nondiscrimination (do all qualify) and TIL (late charges).
You can PM me if you want further details.