Conservative and low risk. 

Another example of this is Newark, extremely strict laws making land lording a second job.When finding the right area to invest, towns with more lenient land lording laws and proximity to public transportation tend to be a receipt for success.  

Let brokerage grow, tenants pay down mortgage, and save up for another property organically (Cons - slow growth, waisting equity// Pros - low risk)2) Cash out the $300k brokerage account, pay off the townhouse, start cash-flowing $2,400/mo, and save up for new investment or 1031 into multi family(Cons - cap gains tax on cash out, high Oregon income tax penalty, hard to find deals being $2,400 monthly cash flow) // Pros- cash flow, increased leverage into large investment)3) Cash out $300k brokerage and put into separate Multi Fam property, hoping for $2,400/mo+ cash flow, keep townhouse rented as is (Cons - cap gains tax on cash out, not utilizing equity PROs - increase portfolio value, higher upside with value add or rent increase on new units?)

In my area, they charge transfer tax on the assessed value rather than the LOW sale price.

You might be able to find a lower price point per unit than I’m at but it’s a LOT MORE WORK to have low quality properties as opposed to nicer ones.

This vary heavily town to town. 20% down is great if buying strictly as investment but if you have a way of owner occupying I would explore that route and apply the 20% down to increasing value of property and instead using low money down loan. 

I have lumber liquidators, home Depot, Lowe's, and who knows what else near me (central CT).

Case in point, years ago we used Olympic paints from Lowes, which were carried for a long time.

I'm not too familiar with the markets yet but research I've done suggests that the towns of New Britain, New Haven and Hartford all have a good mix of inventory and low prices coupled with plenty of amenities, night life, cafes, etc and local colleges to bring younger people to the area year after year.

I appreciate the reminder as well that if the gain is fairly low then it may make more sense to just pay the capital gains taxes now versus 1031 exchange.