most of it cookie cutter contracts. buyers can look on realtor. com.  

I'd like to believe that Portlanders don't conform to cookie-cutter standards (i.e. the notion that everyone wants a nice car and a 3/2.5 home with good schools), and that getting Portland right is about knowing the different neighborhoods well and targeting a specific niche (e.g. maybe secured bike parking and a rooftop garden is more important than a garage and a yard), but we might still just be like everyone else.  

However the defined rules and strategies don't always fit like a cookie cutter.

So my advice: understand your market and local regulations, avoid the average cookie cutter STR home, make your home STAND OUT and be aware of the significant upfront cost needed to do so, and absolutely hire a local PM company.

1) I'm a bit biased, but i recommend you reach out to a broker that specializes in these loan types. you'll find that there's a broker/ mortgage lender on just about every street corner, but many of them (i'd venture to say even "most" of them) stick to the cookie-cutter type loans, and don't have a good understanding of the investor side of things. there are lenders tailored to your BRRRR strategy. you won't find them by calling up Loan Depot for example, and many Loan Officers will try to fit you into their box.

It's a step they are apparently legally required to take but the system is obviously quite rigged.

Other's think that it's a casino rigged by the powerful, and only fools invest in it.Which is true?

No, you want the basic, universal, cookie cutter floor plans, so there’s no emotional benefit for it.

I realize you have a big rig here and parking it somewhere was difficult.

If you were trying to say that the real estate brokerage business is rigged, I agree, it is the system we have, but it's the American way, learn to deal with it until you can influence law makers there is a better way.