@Tony FerreiraYou have good options based on the limited amount I could gather based on your post.Shot you a DM, please feel free to follow up if you'd like!

Feel free to reach out anytime!

Your running a business and the house has to be cleaned wether you pay someone or do it yourself and work for free and cheat yourself. 

However, don't shy away from Portland if you find a great deal that aligns with a house hacking approach.Feel free to reach out if you need more specific insights or connections in either market.

Yep that couple got part of their gain tax free and part was indefinitely deferred (till they died) then it was tax free to their heirs - not a bad gig. 

I will make thing easy for you.This is my actual real live assumption.Prop Price=$560k , interest rate=3.3%, capital gain tax for invstment=33%, appreciation=5.75% , slightly positive cash flow (DSCR 1.05).Result after 10 years:Return after 10 yearstotal_net_PITInetReturn Factorcapital gain if OO$577,851-$385,000$192,000(live for free)1.6capital gain if rental,positive CF$381,000$26,000$407,000(still the biggest buck)3.391666667caiptain gain if rental , negative CF$381,000-$24,000$357,000( not that bad really)2.975so rental property with highest appreciation and bit cash flow at the end of 10 year is still performed better, even negative CF is not that bad, the return from original investment after 10 years is still almost 3x.

Start with BiggerPockets Ultimate Beginners Guide (free).

The turnover is not free for you either.

I do free live trainings on thursday.

Recently I heard an online property insurance company advertising on one of the BP podcasts, but I can't remember what the name of the company is.