The expense of having a qualified and seasoned CPA who has fought with the IRS for the rights of tax filers can not be under-estimated.

I hope to meet some seasoned investors and get this started.

Not even all DSCR lenders will allow this because most want to have 60 days sourced and seasoned funds for down payment, closing costs and 6 months reserves.Even though you don't qualify for traditional financing, you may qualify for a DSCR loan, but you definitely need a broker to help you structure the moving parts.Stephanie

@Everett Morris contact your bank and  also smaller  credit unions and bank in your area  and  ask for a personal LOC ...rate  will be  high  if you qualify and  you  likely   will need  to pull  funds  out and  deposit  to your  account  and let  season for  2-3 months   before you  can  buy another property

Which of course is a very large range, but given the seasonality of short term rentals, the average monthly cash flow over the course of a year will likely end up near the middle of that range.In the most conservative case, if I long term rent the top unit and mid term rent the basement, I would estimate around $4,000/mo for the top unit and $2,200/mo for the basement unit.

For example, many hospitals are doing "seasonal" contracts internally.

Get someone in there for a few months and get through the winter season, then put it back on the market in the spring and look for a one-year lease.

That was my largest concern, was how quickly I’d get it rented out, especially during the holiday season.

If I do not have a W2, am I still able to refinance into a longer term mortgage after I season the property? 

If I do not have a W2, am I still able to refinance into a longer term mortgage after I season the property?