Hi @Joshua Berube interesting series of events and read.
PJ here and I buy, fix and flip properties in Vancouver BC through our Property Investment Group and profit share with investors also. Yes it is expensive here but returns per project are great! I also have bank financing on projects at 70% so this helps.
Interesting to see how the Ferry plays out but as some have mentioned go about your project as if it has no impact. There is always demand for good rentals and properties with something unique.
I'm a bit anal with details and numbers so always go into deals knowing my costs before I dive in and in this case knowing what I can build with the city (fourplex and max FSR), how long their wait is and add on 50%, cost of building it, cost of holdings etc. As you mention speaking and finding a lawyer who has done what you need time and time again is important. I commend you for your bravery and smart with lease option. You mention what if the owner defaults on payments, but couldn't or wouldn't these be with a lawyer in trust? I don't now much about lease options but sounds like a "seller financing" type situation.
Just remember time is money on your project so no wasting time and if the city appointments are booked up, when you make an appointment make another two in advance at the same time say 10 business days after the next. This way you have time for and drawing or plan amendments and questions you forgot to ask come up. Personally I have found that permit officers are very vague via email and just send you links to stuff that is relevant but not specific to your question.
Also when pitching investors think what do they care about: They care about you as a GC getting the job done, your reputation - do what you say and say what you do, financial cost and expected return & timeline. I created a PDF portfolio (happy to share it with you for idea) for the bank and investors that gives a lot of info about us, who we are and what we have done. You could add pics of work you have done or managed in the past and what you are doing to educate also.
Out of curiosity I will be looking into some properties in NA to see if buy and hold makes sense for positive cashflow even for some older places. I like the town and use to travel there for work. Maybe @tom stromer can advise me.
Look forward to more info...