What I would do when beginning my journey is assess my current situation and goals.Are you open to owner-occupying your first investment?

We just closed a duplex for a VA buyer yesterday and this was the same situation they were in so we had to actually sell their first home to open up the entitlement capabilities to then buy a better property that they will occupy for 2 years, then move to the next project. 

For example, Denver county strictly prohibits non owner occupied str's but have no restrictions when it comes to MTR's in the area.

I just purchased a rental last month with a tenant already occupying the property. 

And what does that do to my contract and owner occupied requirements of 1 year?

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?

Some neighborhoods in Multnomah county anre owner occupied only as well. 

We help owners sell tenant occupied properties to investors all of the time in Reno. 

You owner occupied this condo for 2 out of 5 years? 

I'm unsure what the right path is, but I've been reading about investing in owner-occupied, multi-family properties.