So the soft sell may work... and would also give me more wiggle room to change the price if the market has softened.

You could always sell it.Typically, you should be talking to lenders in advance of even buying the property so that you know you'll be able to refi.If the market softens and the appraisal is lower than you current estimated ARV, you will still be able to refi, but you might not be able to pull out "all" of your investment $s.

What happens when you combine rising interest rates with softening rents as we're seeing in some metro areas and debt that expires in the next few years?

So much can go wrong- major repair items that you've missed, the market can soften, vacancies, inability to refi, etc.

A department of our business is wholesaling and we have been ramping up that department due to the softening in our market on the retail resale side. 

Yes, prices have softened, but being based in Union county taxes vary greatly.

You will start hearing or probably have already heard that the market is softening a little bit. 

The higher end (> $4 mil) has softened, but starter SFH’s in the cheaper hoods ($1-1.5 mil) are still selling like hot cakes.

The other part of me is questioning if I should wait 9 months, save up some more money and continue learning as much as possible to see if the housing market softens up to get into a better deal. 

We've seen out-of-the-norm price drops and and the winter months can be tough.Seems like there is a softening of rental prices coming.