My land is also buildable and I have plans from an architect for a 3 bd/2 ba home which would cost 300k to build (it's in CA) and is in an excellent STR location...but I'd need a construction loan to build it.

If I can go with this plan.

Building new sounds great, but it's usually way more expensive per square foot when you factor in land, materials, labor, and permits.

I plan to hold it forever, letting tenants pay down the whole mortgage.

Clackamas county (slightly less expensive) or Washington county (intel,Nike,Apple,Microsoft) these tech companies have increased the cost of living and house prices  (it’s higher than downtown pdx) but the neighborhoods are good and safe. 

I am almost completely through Planning and permitting.

Do you still live in it or plan to move out?

No expensive hobbies other than the kids (I play disc golf and I like to do wood working).

I have a 3 flat in Lincoln Park, Chicago, IL that I am planning to list for sale in the next 3-6 months.Currently owner occupied in 1 unit (Duplex up, 3 bed 3 bath).The other 2 units (2 bed 1 bath each) are rented.I am wondering if it is more attractive to buyers to leave the 3 bed 3 bath unit vacant when I move out, or should I place a tenant in there and then list for sale?

For the newbie investors, buy something that cash flows and plan to hold it for as long as possible.