Not sure of my preference   Just different.No one can predict storms, but if you schedule in hurricane season you have better chance of hurricane than if you schedule outside hurricane season.  

Can be hard to tell whether its a true downturn or a seasonal slowdown though. 

In addition, be strategic about when they would stay - don't give away premium nights during your peak season for this.

Traction is cold hard cash money seasoned in a bank account.Cash Accumulation is the most needed thing for many people.

In our welcome basket we allocated $2-4 for gifts i.e. chocolate bars, Florida Oranges when in season, etc

One, is dynamic pricing a thing for mid-term properties without much seasonality?

I do a mix of STR and MTR in Tucson ( STR for peak season around gem shows ) and MTR during the other months 

It's possible you could take the loan to another bank that is willing to do purchase plus rehab, but there is likely a seasoning requirement.

The Front Range market has a very pronounced seasonality to it: March-June is "selling season" when the bulk of the listings hit the market and all of the retail buyers are out hunting.

I’m nervous as I watch the clock tick further into toward the winter season but I didn’t want pets for a reason and I will hold firm.