Boss Rods, I bought the '33/34 premium roller from N&N when I retired and started working on it using Speedway, Summit & others for parts sourcing, along with lots of trips to the local hardware store, metal shop, etc. A now long gone magazine, Street Rod Builder, had done a four part series titled "The Low Buckaroo Coupe" (or something like that) starting with the N&N premium roller, and targeting a completed car running in buffed out gel coat (no paint) for $35,000 using a new crate engine & tranny. When I was trying to figure out what to buy I visited with a fellow from Oklahoma that was driving a basic highboy '34, and he thought that a fellow could get one done for the range of $27,000 to $30,000 doing everything himself, using a junkyard powertrain without having to rebuild engine or tranny. I went overboard on the power train, which blew my budget, but I did essentially everything myself other than having the engine built. If you want to scan through it, my build thread was pretty complete - Followed Me Home, '33 Build
Having all of the tools on hand, or friends who have them and are willing to let you share, is a key to shaving costs. Any time you pay someone else to take on a task you're now on their schedule, and at their mercy for the costs. Given your explanation of what you'd do and what you'd farm out I'd say you'd be hard pressed to get the roller package running for $30,000 but that's just my opinion, not knowing your detailed plan.
Another tip, I looked at a LOT of options, and I decided that N&N gives the absolute best value package that you can buy. Others are cheaper, but you get less quality, and there may be some that claim better quality but you'll pay through the nose. I'd go back to N&N in a heartbeat.