I am just starting to do the research into shipping containers and your guidance will help me continue or create a new path.  

Hard money is straightforward.

Paperwork is fairly straightforward.

It's pretty straightforward outside the web of nonsense the salesmen spin about it.If you're in the residential renovation business for the long haul, window replacement is one of the things that comes up again and again.

. - Inspection is done by the city/township, so as long as you're working with a licensed GC, it's fairly straightforward; it'll just have more line items due to extensiveness of damage that has to be remedied. - Also, most Restoration/Renovation companies that specialize in rehabbing fire damaged properties will use a web based tool called Xactimate for a comprehensive scope of work, which may at times be, as long as 300 pages.

There are not very many people that have developed pocket neighborhoods in Portland, but if you want to talk to two of the best then I would try reaching out to @Mark Desbrow at Green Light Development who has done two pocket neighborhoods I believe, as well as Eli Spevak from Orange Splot who does amazingly creative work and is also a pioneer of pocket neighborhoods in Portland.Currently there is a proposal in Portland called the Residential Infill Project that seeks to provide a path for more pocket neighborhoods to be developed, but it is a rocky road and some of the latest versions have really dwindled down the policy's potential effectiveness.If you want to check out another great pocket neighborhood while you're in town but want to escape Portland go to White Salmon, WA in the Gorge.

EtcI don't think either path is bad, but there's a lot to consider.

Wild card: is there a middle path I am missing that would generate good cash-flow at low starting capital that works either while i still rent or takes me out of having to rent?

Their permitting is fairly straightforward but if you are changing zoning, you may face unpredictable outcomes during public hearings.

Often referred to as the "6th Borough".The food scene is outstanding.The Path train from JC has 4 locations.