As has been discussed ad nauseum, you will want to make sure code allows a short-term rental wherever you are buying.

In terms of your comment "a lot of investors you may be competing with are goign to break even or even have negative cash flow initially". 

If you can't be competitive on price, be competitive on terms. 

I would stay away from long term contracts and pay by the month to start if you are using a service and then after you have real world experience with it, you can sign on for a year for the discount.

If the buyer's strategy is to hold long term, and they are getting favorable interest or payment terms, and the value supports, offering more than ask isn't necessarily a bad thing for them.

REO so negotiating was limited to bank terms.

Are they all long term?

All of my long term rentals are managed by a company; I have one property in my hometown and 3 properties OOS. 

There’s a lot of misinformation out there that is presented as knowledge.One can do a reverse exchange where one buys the new property first and then sells the original property after - all via a 1031 process. https://www.investopedia.com/terms/r/reverse-exchange.aspReverse exchanges do exist and they are “legal”. 

Does anyone know of a software to calculate medium term rentals?