I'll be starting back school in Fall for architecture and will need flexibility as well.

I am an architectural designer and contractor and my wife, @Heather Hopkins is a realtor in the bay area.

These architecture, engineering, and city fees will add up to $10-$15K easily.

I do have a BS degree in drafting design architecture as far as that goes. 

For me its all about the History and architectural details.

Affordable rentals and home prices, along with cafes and architecture from the 1800's- what's not to like?

Everything from the brickwork to the architecture is just different...  

Examples: properties in areas zoned exclusively for STRs, purpose-built STRs, prime location relative to attractions, views, unique architecture, and other amenities that are time and capital intensive to replicate like indoor pools, etc… That average looking house in an average location you’re looking at on Zillow might cashflow today at an affordable price, but it is wildly vulnerable tomorrow.

Our recent retail building is going to take us 5 months for actual construction.The DP was 4 months (had to get architectural controls agreed to, DDSP- deep services with City) and then another 6 weeks for BP.  

If this city allows this go for it's by far the cheapest.Alternatively, you can pay an architecture firm to draw up the plans.