Say a $50,000 heloc will be assumed one day to have a $500.00 a month payment even though today it doesn't since its interest only and at a lower rate than say a year from now when it rises each time the Fed Reserve raises their short term rate.

It's just how short sales work.

If my plan was to hold onto this short term (let's just say 2-3 years out of thin air), it makes no sense to pay the point up front and I would opt for the higher percentage rate per month.I know I've heard/read that some people would argue that it rarely ever makes sense to pay the point up front, but if its a long term play, I don't truly understand why that might be...Any info appreciated!

Everything that I've seen says that an LLC is best for long term investments (rentals), and an S Corp is best for short term investments (fix/flip).

I am getting a short-term lease while I get to know the city and save up some money.

In short, I'm a private real estate investor.

That was the highlight of my short realestate career,only been in for a few years.

Worse, if you refi and don’t pay it off quick, you will be taking short term debt and turning into long term.

But even these deals feel a lot like musical chairs... buy, force a bit of appreciation and hope someone will pay a lot more at a compressed cap rate in an interest rate rising environment 

Both are short-term positions as I am a trader of those instruments.