For example: We provide tax preparation and advisory services to people who invest in commercial (including multifamily) real estate, and high w2 earners investing in short-term rentals.

Is it high appreciation area with a low rate mortgage?

So, your focus may need to pivot from high rental cash flow to little to no cash flow as a rental with an appreciation upside.I would recommend taking your $150K to $200K and securing a solid equity position in something that will cover its expenses and maybe provide a small cash flow, but then is poised to appreciate nicely over the course of the next several years. 

Not to mention sky-high drama factor.

I feel as though my home is priced too high, however, my property manager insists the price is competitive.  

@Micah Huffman unless you are going to commit to learning some basics about being a landlord AND are willing to commit at least 2-4 hours each month managing a Property Management Company - it's probably best you sell.Otherwise, it's highly likely you could lose more due to bad tenants and management.

In high-appreciation markets (e.g., CA), lower cash flow may be acceptable.

Look for properties with high cash flow potential, good condition, and room for improvement, such as value-add opportunities.

If what we are feeling is accurate, the January data should show substantial increase in buyer demand.Jan 1, 2020 to Jan 1, 2025 InventoryWhile interest rates remain high, the demand from buyers is still strong.

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?)