Technically my job isn't requiring me to move (I can be based out of anywhere), but moving to another city with better transportation would improve work efficiency. 

It is technically a pile of assembled building materials.

Technically, it wasn't on record as a 3 bedroom, but it had all the features of it.

I've seen properties that were condemned due to a earth slide and need $500,000 of geo-technical work.

I think you should just be up front with anyone that is going to be subleasing from you to keep things clear... they're technically your tenants, not your friends, so run it like the business it is. 

Technically can do it every 6 months if you want to.

You will need one regardless of what structure you use, so ask.If someone gives you money with the idea that you are going to do all the work and give them a profit, then you have technically created a security, and would need to use one of the SEC exemptions under Reg D. 

I realize it's probably not a construction loan, since technically there's no new construction.

Technically speaking an 1850's house in Mass isn't even that old to be honest. 

Not sure if this is the right place for this but it technically is a lending question.