I am interested in utilizing space again for group meetings, workshops, and for clients who may still desire private space.  

Opt 1) utilizing our savings in the brokerage account and emergency fund and pay for it all up front. 

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?)

Meanwhile pay little or no taxes utilizing depreciation.

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

Additionally, do you all generally use a smaller income criteria if the rent is inclusive of utilities? 

Can you share what main use case that you propose to utilize our solutions would be?

@Trevor McCormick to piggyback off what others have said, determine if you are trying to maximize it as an investment or utilize it as a vacation home you will STR to help cover expenses, as this could dictate which type of property you are looking for. 

Finding tenants is the big one -- we have the tenants pay for the maintenance & cleaning out of their utility payment. 

paying mgt any landscape/snow/utilities?