Where to go? Reno? Bend? Salt Lake? Oregon coast?

[Bryan Begun]

We need to generate some more cash flow in our lives and we can go anywhere. But where to go?

I like surfing and she likes skiing in the mountains. 

We have three rental properties and they are in Sacramento, CA, Boulder, CO, and Newport, OR. We should consolidate but where?

Most of our family is in CA and one of our criteria is to be 1 day or less drive time from them. So we will eventually sell and part ways with Colorado (where we live now).

I've scoured the following markets: Reno, NV, Salt Lake City, the Oregon coast, Bend, OR, Sacramento, CA, Lake Tahoe (CA/NV) and touched on most places in between. I've put 4000+ miles on the truck in the past two weeks (and more last winter) driving the western US and window shopping many towns and markets. I love walkable towns with great vibes and vibrant communities.

We are looking to buy multifamily properties and get away from long term single family rental houses. We'd like to try a short term rental but the Oregon coast and Tahoe (two places I love) are extremely restrictive on doing this. Reno makes sense from a tax and insurance and economic growth perspective and also proximity to family but it's not a place I've fallen in love with despite spending two weeks there (one week last winter and one week more recently in the summer). On paper Reno is the best fit. In person its a place I could see maybe doing an investment or two in but its not where I really want to set up shop (I mean that literally; set up a home and also set up a wood shop - so I can build custom cabinets and stuff).

If Santa Cruz, CA ever goes on sale then I'll go there and suck it up with CA laws and cost of living, but for the foreseeable future it is not even a remotely viable option; I looked at a fourplex there generating $10k in monthly income and priced at $2,700,000. 

I do most of the work on our properties myself so any advice about investing out of state for better cash flow is not my jam. My jam is to build and improve to get better equity and cash flow through value add. 

So the question to the community is this: where is there a decent supply of multifamily properties, investment properties, and also nearby amenities such as the ocean or the mountains? Where is that vibrant community of wonderful people and walkable neighborhoods? What are the easiest places to fall in love with where one might also flourish doing a little real estate investing?