We could take the money and apply some of it towards our personal residence to reduce the time required on the loan but there would still be a sizable amount of loan so it really wouldn't make a huge difference in terms of the length of the loan...not a great idea.  2).

I have some properties in mind that I think would work well (both short and long-term) but I don't have money for down payments.

If you are interested, we have an in-person event coming up this Saturday where we are diving in to AirBnB / Short-term rentals in Chicago. 

Yes there are hard money lender that will lend up to 75% ARV and will finance the entire deal to include closing costs.The term is typically limited to 6 months and you will have to extend if you can’t exit within this time line.

I'm not having any luck selling it so I'm thinking of pivoting to a midterm and short term rental as a buddy of mine has had some success with his house in Paris Mountain and the 09 zip code in Greenville.

there are many long and detailed threads on this company. 

As I move purchase price and terms around as we negotiate, at what cash flow amount would you pass on the deal?

"Long Distance Real Estate Investing" by David Greene is a good options and will help with getting an idea of good markets all over the place, not just your own backyard. 

Sharing a kitchen probably isn't a big deal for a short term contractor.

Financial goals: Our current jobs provide for high-income but not a lot of time for active real-estate investing, so our strategy is long-term buy-and-hold with less headache properties.