Our Summer dates still fill in even with less than 7 day min stays.

Most of our rentals have desired move in dates of just 2 weeks out.

In-unit laundry is a must-have, and high-speed internet is essential for your guests, especially those staying for work purposes.

I am not sure they would be comfortable with me blasting their contact info all over internet. 

Figure out all the extra expenses of utilities, management, perhaps hot tub, internet etc. go low on income and high on expenses and see how the numbers look.

The other has experience with real estate with multiple units, however, is way behind on up-to-date systems and technology. 

This is the internet, so it's forever, and you're looking like a damn fool.I am an open book.

Bird dogging may have been more popular before the internet, google maps, etc.

Common reasons:1) Change of closing date (instead of closing end of month, if it gets pushed to beginning of next month, prepaid taxes, interest and insurance will increase because you have through to months end)2) Appraisal comes in low and LTV goes up.

And, just like dating people, even if you both WANT to get married, that doesn't mean the first person you date is going to be your future spouse.