Permitting can take anywhere from 60 to 180 days depending on design of the ADU, the configuration of that lot, environmental conditions, and other related development issues and matters.

The type of home (SFH,MFH,HOA involvement, etc.) and the configuration of the property (adequate space for the needs of the animal) will factor in.

I've created scrips for them to follow and have configured the call forwarding to ring their office prior to tenants reaching my voicemail. 

With the short stays it is hard to make money with this pool.How do you determine critical information like the right rent range to target, property type, and configuration from the other side of the country?

If you can't find a configuration with yourself, dad and/or mom that passes muster you'll likely have more success just getting a commercial loan. 

The ability to take several parcels and re-configure them in a way that should triple my money even if I just sold the lots and did not develope.

If you can prove the property was in the current configuration prior to the 2001 UDC update, and the zoning is not correct for the current land use, then your property is considered "non-conforming" subject to the underlying zoning. 

Also the configuration doesn't look like it would work.

Never seen one split for multiple tenants either due to the preexisting configuration but hopefully the demand in your market will help you determine the best way forward.

On that size house I would expect something around $5k, depending on the configuration of the house.