My first thought is check with the city zoning laws and permitting to make sure this is possible.

Permit timeframes are long and I'm looking to flip the home. 

I did not get a permit or a CO for either.

I'm not sure I have a great suggestion in regards to best ROI for you.However, I've done projects in Waco and done permitting for commercial projects through the City and know surveyors in Waco as well that may be required if you plat into new lots. 

I cannot find a site where I can enter the parcel number to see if STR is permitted.

Fairly certain one could not get a building permit for SFR if there was a landfill below it.

San Diego has some spotty regs here and there plus it requires a permit of which there are waiting lists.https://www.sandiego.gov/treasurer/short-term-residential-oc...Check the address against the zoning and read those regs to make sure you can do it at that location.

What's the permit plan and getting it separated?

It's a thrilling and rewarding world, but it can also be overwhelming for newcomers.

The home as an existing, permitted ADU above the garage which my fiance and I live in.