Goodmorning Sandy, are you thinking of smaller or larger unit multifamily and are you thinking of investing in Oregon now?

If you did sell I would 1031 into something larger but you'd have to see if it'd beat your current property. 

Quote from @James Wise: I've never heard of KS York so I've got no dog in that fight.

Hard to scale on these larger deals Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

For larger jobs, in quarterly draws.

STRs require more hands-on management, but it’s a viable option for reducing your taxable income without needing REPS.You might also consider a cost segregation study to accelerate depreciation on the rental, creating larger upfront paper losses.

If you use an FHA loan as an individual, you’ll benefit from a low down payment (3.5%) and more lenient qualification requirements, but you won’t have liability protection, and the loan will stay in your name when it becomes a rental.Using a conventional loan through an LLC offers liability protection and scalability for future investments but requires a larger down payment (15-25%) and often comes with higher interest rates.If maximizing cash-on-cash return is your goal, FHA might be the better starting point.

I accepted the family with a larger security deposit. 

Are you looking to increase cash flow with every sale and purchase or keep building equity to buy a larger property down the road?

Or even purchase something larger such as multi-family or commercial that provides better cash flow.