I'm a bit baffled by a few things here.To begin with,you could buy a more or less equivalent Yanmar diesel for a lot less money and come out way ahead on operating costs vis-a vis an outboard,particularly with the distances you propose to run the boat.
Yanmar 4LV250 Marine Diesel Engine 250 HP https://rapidoengine.com/products/Yanmar-4LV250-Marine-Diesel-Engine-250-HP.html .Yes I do realise that no sterndrive is included but I don't know of any experienced users who would take a sterndrive over shafts,or you could probably have an adaptor plate custom made and still come out ahead.
Try ordering an engine from Rapido and see if it ever arrives. I checked with our Credit Card company last fall and they won't even process any payment to that outfit, nor will the bank wire any funds to that account. Any new US Tier III diesel that's going to be USCG documented (since 2018 for recreational) generally has to get setup & commissioned by a dealer, and the engine won't be supplied be some website with a fake or no physical address. There are dozens of those websites...the clue is if you see a new engine listed with a price, it's probably a scam. That engine you're looking at is more like $47k plus more for stern drive / straight shaft output w/ gears, prop/s, controls, commissioning, dealer fees, etc.
Can you get a used Tier III diesel? Sure. Will it be any cheaper? Maybe, maybe not in the long run. "Hurricane damaged" engines from Florida are fun....That's a code phrase for "engine submerged".
Any Tier III will typically run at higher rpm, will have common fuel rail / turbo / inetrcooler. Their expected lifetime is much lower than the really good older, slower RPM diesels. No, you can't just use an old truck or tractor engine (and marine heat exchanger) like the old days. I know, I've done a boat or two like that back in the day. I've got a stack of current marine diesel quotes from Yanmar / Volvo / Merc / John Deere / Cummins / Steyr / Iveco / Cat / Cox outboard / Oxe outboard. I feel like I have a handle on current Tier III marine diesel engine prices whether it be sterndrive, v-drive, IPS, straight shaft, diesel outboard (diesel outboards are at the extreme). Yes, cheapest option for diesel would be a 80 or 110hp Yanmar that would be a good fit for a full displacement trawler straight shaft setup (like a DIY strip-planked Robert's 29' TY, mid 30' Coaster series or similar) - maybe around $30k with engine, gears, controls, shaft, prop and $1200 commissioning fee. We also have to look at what service is available along inside passage - From that angle best options are Deere / Cummins / Cat especially if you have a legacy 2000 RPM engine in an older boat. Yanmar you can get parts for along the way, maybe...depending on what's in stock. Or you might be waiting several days at the boatyard waiting for something to get flown in. THE OTHER THING TO NOTE is all Tier III engines will require a shop to have whatever proprietary software to access the engine's control computer to register any repair or changes to tuning setup (same goes for newer outboards as well). Now your repair shop choices are more limited along the way. Diesel engines last longer but I can easily replace an outboard many times over for less money. Right now diesel costs a little less than gas, I know. There is no 100% correct answer. Would I rather have diesel? Sure. But the resell value of the boat has to still be something to consider. If you build a boat sometimes you're lucky to get half your money back at resell time, but we do it for fun anyway.
RE: Just making a physical model instead of CAD way of visualizing the real hull to plan changes: Turns out that's really the fastest simplest way. In a few hours with some posterboard, scraps of balsa and tape I've setup a basic model of the boat. 1/10th scale, so about 36" long. You really get a much better sense of the boat that way, much more than anything on paper or CAD. If I wanted to I could create a regular table of offsets from that, and generate a fairly accurate 3D CAD drawing. BUT we looked at the boat for a while and decided to cancel the project...too long and skinny especially if we add on extra length for outboards. Yes, it's a trailerable boat which is sort of what we're after but we're already setup with the means to tow up to 11' wide and 22klbs, so we'll probably look at building a boat with more beam, and just use regular cold molded technique. I think stitch & glue has it's place, but for us as the boat gets bigger other methods work better for us.
Thanks all for the advice!! - Yes just making a physical model is the way to go if you want quick results, at least for me.