Assuming you like both rods identically, I would look at which offers the best savings/value right now? When I'm buying used tackle in general vs. new/discounted/closeout from a retailer, I am all about being an opportunist.
As far as "babying" a rod. Fish it, that's what it's made for, but do so in a responsible way. Here's a good read to help you avoid breakage.
How To Avoid Breaking Fly Rods | MidCurrent
When I buy used gear, I want to see good detailed pictures BEFORE I make a purchase online. If I'm buying from a seller local to me and I have the chance to look at it before I buy, I'm looking for nicks, chips, anything that could make the rod break. If you have to send it in for repair, deal with it IF/WHEN that happens.
Last but not least, if there is a rod you find that you "can't live without", if you are patient and can wait, you will find one. I can't tell you how many different discontinued Sage rods regarded by many as "best ever" rods I've seen up for sale. Patience is the key here.
P.S. It really sounds to me as though you want the Winston. If the rod is in good shape, the price is right and within your budget...go for it.