I can understand your point, Michael, but when you come home aching all over for weeks on end every summer, seven days a week because you had to use all the sunlight there was in the day, and the physical exhaustion shuts down your brain no matter how much you wish you could keep thinking, I don't think it's quite the same thing. 

But the city has increased their effort to shut down unpermitted STRs by a lot.

I hope I'm wrong, but when the company shuts off the phone and fails to deliver on the "updates" they promise.  

It's this new reality that caused a flight to these markets, with many people living full-time in what used to be vacation-only markets given remote work being embraced, and the flight from cities due to a desire to escape the conditions where COVID spreads more easily, as well as escape cities that were decidedly less fun not only due to entertainment etc. being shut down but due to increases in homelessness and general blight.If COVID disappeared tomorrow, everyone had to go back to the office, and international travel picked back up to normal, it's hard to see how these markets wouldn't get hit pretty hard. 

He's Captain of the Morale Suppression Team, but his tax knowledge is extensive.if anyone remembers Joe Gore  when I first got on here he called me out as a FAUX HML  I proceeded to show him over 1000 fundings.. that shut him up.

I took the offer from a flipper friend of about $70K and shut the offer off  early thereby rejecting the offer of $72,000 by the adjoining property owner.  

I have shut that business down and refuse to do anything but get the absolute best price possible for a buyer or seller I represent as an agent.

Seeing as an S-Corp is a passthrough entity (via your Social), and assuming that income has already been taxed, I'd shut the S-Corp down, dissolve the corp,  and transfer funds in to your personal account.At that point ~ you have a much better shot of getting a loan/funding via going the personal route, over a failed (or no longer bringing income in) ~ advertising S-Corp.I'd find a Local RE Accountant or CPA ~ Go over everything with them, and see what they may suggest :)

I posed this question because my initial thought was to keep learning through the winter then hit the ground making offers in spring, but didn't want to shut the door on any opportunities in the winter.

It may be that your roofer is wrong, but if you're getting shut down on a claim you should get a second opinion.