If I go through the city and get a proper one, I'm told that they may not give it on a smaller lot like mine (I will investigate) and also I may be opening a can of worms since the GH was built here decades ago.

Do you have any tips on how I can properly analyze my deals effectively?

My biggest question is how do you typically get a sense of the ARV for BRRRR when predicting how much all-in to calculate the proper LTV?

I don’t have anything lined up but I was planning on trying to obtain a construction job for the time being for again the income but most importantly the knowledge of how to do most jobs properly.

I had my contractor paint them (inside and out) with a higher quality enamel cabinet paint after proper sanding and other prep.

As far as money and structures goes,  look at strategies using Options, Master leases,and Subject to purchases which can all be used will little cash if done properly.  

Fine clays and mainly silts are problematic because they could be dormant but when water finds them then they react, expanding substantially therefore the failure of foundations. 

It is especially important in multifamily so you can properly underwrite the property.

I am totally willing to look outside Portland proper, and might actually prefer something outside the city because it seems the regulations are a little more lenient outside of Multnomah county.

Whatever your choice, cleaning, maintaining, and storing your sprayer properly will save you a ton of headache in the long run.