Morning Nathan,
Congrats on exploring a big jump-it takes courage to buck the news cycle and confidently reach for a bigger future!
I have answers to a few of your questions while I’m sure spec builders here can chime in on their end for you.
While Portland may not require parking, I would strongly consider it if you’re thinking you’ll sell them individually as condos, especially in the Jade District. Yes, you’ll have good transit access along 82nd but I believe you aren’t as likely to attract the car-less owner there as you would closer in. 82nd is changing, but I don’t think it’s happening fast enough to justify leave out permanent parking if you’re reselling individually. You’d be more likely to get away without parking for tenants but even then, what kind of tenant are you going to attract? If your target tenant is looking for a car-less lifestyle then you’re going to be competing with units close-in so you’ll have to win on price or features to get them out to 82nd. All that being said, it might not be worth the cost of putting in parking, just be aware on the front end that you’re reducing your end buyer/rental pool by not having it.
Have you comped our what four condos will sell for vs. two duplexes? While you don’t have to decide this instant (you could always convert later) it’s good to have an idea of the market differences between mf and condos.
As for soft costs, you're looking at a fair amount for a condo conversion-there are legal docs to have drawn up, reviews, surveys, recordings, setting up the HOA, reserve studies etc. There are attorneys who will help navigate the process for you and act as an orchestra conductor to keep things moving along. I've got a lender who is a problem solver and loves geeking out on the minute details of these problems (it's what makes her a great lender) and she could be a great resource for you...she's put together condo conversion workshops with experts all talking about their components. I'm happy to make an e-intro.
The 80/20 rule applies to most things in life but in Portland real estate it’s more like the 90/10 rule...10% of the agents do 90% of the work. The best way to find an agent with the skill sets you’re looking for is to ask for referrals from people you trust or on places like BP. There are a handful of active agents here on BP in the Portland area (including my business partner and I) who would be good places to start. I suggest creating a list of questions that are important to you and start asking!
You said you’re not sure yet what route you’re going to take and I applaud you for doing the investigative work now, before you break ground! One last thought, have you considered just selling to (or trying to partner with) a developer? You’ll make less money but you may learn more along the way for future projects or reduce the headache factor (which can be significant). Not saying you shouldn’t move forward, just that all options should be on the table!
Mathew