One of my investor clients now requires photos of where the prospective tenant currently lives. 

(From acquisition to ready to issue permit)How long will the construction take until finished?

If your tenant is reasonable - have your broker coordinate with them for showings, hold open houses (yes they are permitted in OR with COVID precautions in place).

@Roy Gottesdiener I'm an appraiser in the Tampa Bay area and it's actually not a requirement for the addition to be permitted for appraisal purposes, however, most lenders will then require the appraiser to use a comparable with a non permitted addition or bedroom in order to illustrate the marketability of the non permitted portion of the home.

The key to success in adding a bedroom is to make sure that it is permitted so that it shows in the tax roles.

Is this even a permitted multifamily etc. 

As an auctioneer with family businesses and at 78 years old, I continue to use a program I and teach; POWER PROSPECTING and Control and Roll to hunt down buildings, houses, commercial buildings, lots and land that have a potential for cash flow or equity.

This is because they are not able to get another permit. 

Note I would get these permitted from the town, but not sure if GC work would require contractor license.2) Permit process question.

At that time, I had no real ideas or prospects to carry me over such an issue that we face today.