BiggerPockets also has a calculator to analyze deals, and I highly recommend you start this as soon as possible, even if you are not ready to buy.

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?)

I would highly recommend you listen to all the podcasts from Kenny Bedwell - Cashflow Positive.

In San Diego at the current rates for a purchase loan (which has better rates than an ADU additions) at high LTV, I show 1% does not cash flow on a sustained basis.  

Quote from @Tod DuBois: Looks like everyone is using some software tools for various tasks, I'd not heard of most of them.

Specifically the area I marked in yellow.Any help here would be highly appreciated.Thanks!

Prices are high, regulations favor tenants, and finding deals that truly pencil out can feel like looking for a needle in a haystack.

You also need UX, support, quality, a million other things.

@John Sherwood The areas you mentioned are certainly high-demand areas, but they come with challenges.

I have an outdoor pool that easily have 1k+ people using it every season and I never had single complaint due to the water quality.