Business Valuation & Reorg Questions

Hi All, This is the first post here, but I have enjoyed all the content tremendously.

I'm in the early stages of evaluating my first acquisition, and one deal has stood out. As I've reviewed everything, a couple of items come to mind, and I was hoping to get some feedback from the group.

1. The business has about $300k in annual revenue, and the purchase price is $275k. However, the current owner only cashflows $10,000 annually. Are there legitimate levers I can pull (and defend) to question this valuation and see if there's movement on the price?

2. Based on the IS, the easiest way to 8-10x their current cash flow is to reduce FTEs and streamline some OpEx costs. On paper, it seems pretty straightforward, but I'm curious how practical those steps are once you've completed the acquisition. E.g crush culture, lose domain knowledge, reputation management, etc

Thanks in advance for any and all help!