So for the seasoned rental investors...what do you think?

This area of town has mostly older homes (1920s), between 800-1,1200 sqft, and varies between 2-3 bedroom, 1-2 bath.

Is this a dead rental season?

I'm pretty sure it's annual unless otherwise discussed and I know that private lending deals are whatever you negotiate but thought I'd check at this early stage to make sure I'm on the same page as more seasoned private lenders.

I was looking into flipping some properties when I was informed by a realtor about a seasoning period or flipping rule.

For the seasoned investors, should I be worried?

I have a prospective tenant that is a little older that does not have email/internet access and I would need to enter their info and run it myself. 

This downturn is probably seasonal, but the trend overall is up.As always, don't trust the internet, seek professional advice.

Sounds like you should go hard money for the acquisition and renovation and then go with a no income/no seasoning or short seasoning product if you want to make it a long term rental. 

I've been going to Chelan for 40+ yrs but I've only once stayed during the winter months and I wouldn't do it again (Leavenworth has much more appeal during the winter season).Also, the fire season has been trending worse over the last decade or so.