Tail dragger on line with a flying school... be very wary on that and make sure you've got friendly insurers and very good experienced tail dragger instructors teaching in it.
Personally, my advice, if you're looking at something like a cub, take a look first at the various cub-like microlights on the market. RANS S7 Courier and Zlin Savage come to mind, and also the Legend Cub.
Unless you're wanting to do night VFR (or IFR, but really in a cub that's unlikely these days I think) then a micro is going to do the job and make the ongoing cost of ownership considerably less, such that putting it online isn't necessary.
Realistically I don't think putting an aircraft online in NZ is a way to pay back the capital cost of ownership, you are looking to offset (or nullify) the ongoing ownership cost.