I took the plunge a few days ago. I bought a 4bed/2 bath 1822sf sfh with 2 car garage 1/4 mile from the beach, zoned light commercial. Paid 260k. Outright permitted uses in this zone include mf and STR. My plan is to add 2 bathrooms and a second kitchen. I'll live in one 900sf unit with a new kitchen. 3 units will each have their own bath but share one large kitchen.
I hope I can average $30/night per unit year round. 12% city str tax, property tax about 1%. Maybe something like 2000/month net.
There is a bid for new windows, roof and siding for 95k. I think I'll do the windows myself, repair the 15yo roof in spots, replace some of the siding and paint it. I hope to be all done for about 50k. With the inevitable cost overruns it would be fine if it went to 75. Nevertheless I'll pinch those pennies where I can.
One nice thing is Oregon has no sales tax. I've got a new corvette on order so that will save me $6000 vs California.
As for the rainy winters, maybe I'll RV it in Mexico or Arizona.