But I do have my eyes open and am watching for signs of market decline just in case I can strike harder and faster for my investment properties when it does happen some day.

The cultural / political venues are strikingly different for sure.I've lived farther southeast of Jacksonville @ the Atlantic Ocean in  PonteVedra Beach and it all seemed like south Georgia to me. 

This place strikes me as a big loser as a rental. 

You never know when calamity will strike like a stain, rip, or even burn. so be ready to replace as needed and not lose your spare. 

As an alternative, consider taking the profit from your current property and using it to purchase a MFR property that can strike a good balance between cash flow and appreciation.

. ~$256,000 cash to close for both investors)Current rents are stabilized at $1,247/unit per month with utility bill-backs in placeWill be hitting the market after two vacant units are filledProjected year 1 returns assuming a 50% equity position and 9% effective tax rate: Pre-tax Cashflow $13,108 (5.35%), After-tax Cashflow $12,975 (5.30%), After-tax + Pay Down $21,342 (8.71%), and Total Return (After-tax + Pay down + Appreciation-3%) $42,342 (17.28%)These are the highest returns between all properties in these analysisDuplex - 2 Unit Multifamily in Milwaukie$450,000 strike price with 65% Loan-to-value (Approx. ~$166,500 cash to close)Current rents are $1425 and $950 so present upside potential with existing long-term tenantsBeen on the market a long time because its overpriced (list was $535,000, now $495,000)A fairly turn-key property and i have a list of capital improvements including furnace, roof, paint and fencingProjected returns once rents reach full market:Pre-tax Cashflow $6,107 (3.88%), Pre-tax + Pay Down $11,720 (7.44%), After-tax + Pay Down $11,745 (7.46%) and Total Return $24,855 (15.79%)4 unit Multifamily in Clackamas Strike price of $750,000 with 70% Loan-to-value requires approximately ~$234,000 cash to closeCurrent scheduled monthly rents are $1,388/per unit Lots of updates and capital expenditures done, not the greatest location Projected year 1 returns (before achieving full-market): Pre-tax Cashflow $11,489 (5.11%), Pre-tax + Pay Down $21,565 (9.58%), After-tax + Pay Down $21,424 (9.52%) and Total Return $45,291 (20.13%)In high entry barrier markets like Portland, I am finding the small 2-4 unit multifamily properties that hit the market to be mostly priced out. 

While I'm eager to get as many ducks in a row lined up in preparation for that, it strikes me that it may be too soon to start making connections with agents.To cut to the point: If I wanted to walk into a unit in Mid-February 2021, as a first-time homebuyer, when should I start getting with an agent? 

You dont strike me as a very self aware person OP

Question for the more experienced and well versed agents / brokers here: With economic woes striking many communities in the United States, how can you as an agent best provide additional value to someone facing foreclosure?

The previous host could have great reviews from guests, but be one strike away from getting kicked off the platform by the platform at the time you take over.