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eCognition is for OBIA only, and very expensive. You'll need Erdas/ ENVI or other software which can do basic operations. eCognition can handle multiple image for single instance, so no worries. eCongition Developer can even do batch and distributed processing. I used OBIA for vegetation mapping and baseline assessment but haven't tried monitoring. If you can come up with a 'rule-set' for each observation, monitoring should get easy. Before that you'll need the imageries processed and ready. If you have experts who knows python and C++, I would suggest to spend this money on cloud services (ie AWS or similar). Now-a-days there is no point spending money for expensive software and PC, cloud is offering unlimited storage and processing power. Consider this app, Matt Hansen is using App Engine to classify forest loss of the whole world using Landsat image .