The most important thing on your first deal is to keep the risk low.

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.

Everyone has been spoiled by the last 10+ years of low property values with high rents and low interest rates.- Just ask any investor doing deals prior to 2008 Real Estate Crash!

I guess my question is this: is the very low cash flow (due to my low down-payment and high interest) going to improve?

With a low 4.75% rate but minimal cash flow ($50–$125/month), your equity could likely work harder elsewhere.

The low purchase price, combined with an established market demand, made this an ideal transaction for a fast turnaround and profitable outcome.

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?)

Or you can offer a low enough price to make sense.

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