Eliminate debt, establish a budget, and save.

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?)

You could even consider a condo with an established HOA that’s STR-friendly—it can simplify maintenance and management.A Few Other Things to Note: Documentation is everything.

Would it be wise to buy the land with cash we have or utilize as down payment to avoid PMI?

What the gurus don't tell you is that they are comparing market rents to the GROSS amount of S8 rent on a voucher which INCLUDES LANDORD PAID UTILITIES!

So you would spend around $25-$30k a month (this was 15 years ago) on police details and require union gate and non union gate if you had non union workforce as well.In DC area, the utility providers are a huge challenge, whether getting permanent power, or water/sewer service etc - good luck.

I’d also focus on gentrifying areas, as their upside is usually greater than established hoods when the market cycles up again.

I don’t have a problem paying a couple grand to remove some of the just figure it out stage of learning and utilizing expertise of people that already do it. 

Utilizing a wrap he has a mortgage note as an asset to offset the mortgage he’s still responsible for on the property.  

You can expect that you will be required to build roads, sidewalks, storm water control, utility taps, street lights, street trees as well as recreation fees as part of the development process.