@Dan DeGroff - I think you can probably do this as a primary residence since the scenario makes sense (e.g. you travel to Aspen for work during ski season), however, there are some major red flags here that you will need to explain and support during underwriting (e.g.

I'm in Chicagoland and we have what I call a "seasonality effect." 

I think this is the gift and the curse of a still emerging asset class (short term rentals) - as it becomes more "institutional" i.e. more like commercial real estate with more sophisticated buyers then financials and systems for this will likely become more streamlined and stable, but we are still in a place where the buyer pools are more newish investors or typically residential basic investors, so not has experienced or sophisticated evaluating investments based on a detailed financial analysis like more seasoned commercial investors likely would.anyways, just a guess on what might be going on here

It will be not only complex (but doable) to secure financing for it, but the real issue is that if you ever want to sell it, it will be super difficult for prospective buyers to secure financing unless they are seasoned investors which limits your potential buyer pool and potentially your offloading price.

Most seasoned professionals in distressed real estate either transition from extensive careers at real estate firms or legal offices that deal with foreclosures and similar issues.

I see more and more of these gurus with Facebook campaigns of late and know that they are reeling in people that are looking for a silver bullet that is not coming.OK, I will get off my soapbox :)  

A second opinion from a real estate-savvy CPA before tax season can help ensure all deductions are claimed while staying compliant.Good luck!

The "BiggerPockets Real Estate Podcast" is another resource I would suggest listening to for advice from seasoned investors.

However, your credit could also be impacted if you're co-signing or jointly applying for the loan.Regarding the funds, lenders usually require that the down payment funds be seasoned, meaning they need to be in the account for a certain period, often 2-3 months, to ensure they are not borrowed.

Typically DSCR programs have seasoning requirements from anywhere on average of 3-6 months, which means in order to use the newly appraised value, you would need to wait a little bit (although there are 0 months seasoning programs).