There isn't a simple single answer. You will have to read the small-print and ask the right questions. The various shades of buying and selling "Second-hand" might be OK but you can't just assume it. If the salesman tells you his software is an asset ask him directly what that means in your circumstances.
Owning software can get complicated. A simple example: often exactly the same software is licensed differently depending on the sort of user you are. For example student and professional users often pay wildly different rates for exactly the same thing. But it's very unlikely that the terms and conditions will allow the student to profit by reselling his copy of the software at the professional rate. Or even allow the student to use his software for a business purpose. Or allow a business to buy a student license.
You don't say if you are hobbyist. It makes a difference to what's meant by an "Asset". For example, a business 'asset' might have accounting and tax advantages for the commercial owner that won't apply to hobby ownership. Also a business might need a multi-user solution. This requirement introduces another raft of license considerations. Choosing the right multi-user option can make a big difference to the cost. If serious money is involved and you're a business you should buy in consultancy.
Cheers,
Dave