How to approach a condo conversion for 2-unit new construction

[Nina Singh]

I'm new to the BP community and excited to be here! I owe a 8500 sq ft lot in West Menlo Park. I plan to tear down the existing structure and build a duplex using a modular builder. I'm having trouble understanding the steps I'd need to take to convert the two units into condos (i.e. so they can be sold separately). With the high cost of construction it's become pretty important that I'm able to sell these units separately. A few questions:

1) The planning department is unlikely to allow me to split the lot into substandard lots, and so I hope I'm looking at the right option (condo conversion/ "airspace" subdivision). My first question is, is condo conversion the right option to consider here? Not sure if I'm missing other ways to approach this. I'm not interested in Tenancy-in-Common.

2) If my family lived in one unit and rented out the other for a period of time, how expensive and troublesome is setting up a condo HOA and then paying for it every month? I don't mean how it's a pain dealing with HOAs to get repairs done - I'm referring to identifying the recurring monthly costs for such a small multifamily project. I am mainly concerned whether such a small scale project (2 condos) will significantly detract from monthly returns due to HOA dues and condo insurance (which will be negative to start with anyway). How do I find out what those costs would be? Are there other costs I am not considering? This would inform my construction plan.

3) What kind of professional would I enlist help from to 1) Ensure I am meeting all county requirements for this new construction to be eligible for condo conversion, and 2) Help me apply for condo conversion? Should I be looking for a land use lawyer?

Apologies if this was covered elsewhere, I didn't come across these answers in other posts. Thank you all very much!