I'm currently negotiating the form and structure of an LOI with a seller. The business' customers generally sign contracts and pay large (typically 50%) deposits 6-12 months in advance of services rendered. This is due to the business' very seasonal nature with the key operating season only lasting 3-4 months every year. This revenue visibility helps offset the risks of having a short operating season and provides the business with a significant amount of negative working capital. I'm currently looking at buying the business in the off/pre-season. 

The business already is nearly fully contracted/booked for the upcoming season and has a very significant amount of deposits received as a result. The business owner has also prepaid a number of expenses (such as workers' comp insurance) and purchased a number of supplies for the upcoming season that he would like to be reimbursed for. I realize that deposits paid, prepaid expenses, and supplies can all be accounted for in the working capital peg. However, my concern is that these customer contracts and prepaid expenses for items like workers' comp are none transferable and thus the acquisition may need to be structured as a stock purchase instead of an asset purchase? The business also has no real liabilities and seemingly very low risk of any unknown/undisclosed liabilities popping up that couldn't be address with representations/warranties/indemnifications that could be offset against a large proposed seller note?

(1) Are there any searchers or advisors who have experience with a stock purchase instead of an asset purchase? What are the main legal and tax (both short-term and long-term) implications to be aware of? How do these factors typically impact valuation?

(2) Do any legal and/or insurance experts have any guidance on the transferability of customer contracts/pre-bookings and prepaid expenses such as workers' comp? Thanks in advance!