But my market is still better because of my team and our personal enjoyment of non REI.  

If their is a public easement and there are temporary structures within this easement - the city can come in and remove them.

You can househack non-conventionally, but that's by renting the room out and the better way.

In some cases they cannot pull the money out because it is now (Non-owner occupant) an investment and their credit union or bank may cap them at 70% or 75% MAX LTV.Nothing wrong wiht putting 10% down on a primary but look at the rates on both 5% and 10% usually when you have PMI built in the rates stay the same.

(In the simple / non complicated scenario)- time ranges - in the best / simple case scenario how long should I expect this process to take? 

I think I would probably talk to an attorney tbh these business purpose non regulated loans do not have rate locks that have to be honored legally.. they can and do change them unilaterally.. borrower accepts counters or declines and loan fails. 

I just don't like to see the government adding all the regulations and significant costs (those systems aren't cheap) as a knee jerk reaction to tragedies. 

So it's a non-issue if one is good at what there supposed to be good at, follow. 

He has only done single family (non investment) properties.

Must have multi-family zoning and be 500+ feet away from another non-owner occupied STR or you must live in the property for 6 months out of the year.