I’m not unfamiliar with construction, as my full time job is being a field engineer for a civil construction firm (different focus, same industry).

It sounds like you listened to some bad advise on long distance landlording by gurus and guys on here that tell you can do it all with an algorithm .your trying to auto pilot real estate in bad areas from the west coast which rarely works out .

I am in engineering/project management and like my job, but sometimes wonder when can I be independent regardless.

Check to see if you have to install any manholes, fire hydrants, curb, gutter, sidewalks, street signs, street lighting any specific street design or access requirements, Check DOT requirements for access, stop lights and permits, traffic studies, DWQ requirements for permits, permit fees and time framesOnce you have an idea of what you can build and what is required in terms of permitting and infrastructure you want to talk to some civil engineers, architects and commercial general contractors that do the type of projects and build the type of buildings you want to build so you can get an idea of costs, time frame and requirements.This is a brief and broad overview of how the development process works what's required before you get too far down the road on a plan.

He is a rare and magnificent bird when it comes to solving complex algorithms or talking/thinking about complex physics.

If your foundation is concrete slab go with porcelain tile is not very expensive and if you chose the right style it has a upscale character to it, if your foundation is wooden go with a direct installation like vinyl tiles or sheet or engineer wood,

IKEA casework + engineered quartz countertop at kitchen/bath. 

On that note, I am helping identify and prequalify basically all necessary partners in order for this to run smoothly  (brokers, GCs, infrastructure partners, engineers, etc.)- the builder is a high-level guy and does not want to get involved with tedious tasks like learning the market and talking to brokers.  

Another member is a structural & civil engineer, with his own company.

Something simple shouldn't have anything that takes long, unless you're pulling permits and the city falls asleep on you.Otherwise, in a large scale with additions, id say meeting with engineers/architects/builders to plan, implement, permit, and complete additions such as a second story, new master suite, etc.