If say the goal is to reinvest those proceeds into Buy & Hold, how would one structure where to hold the money to reduce taxes?

So, typical options are:1) Come to closing with the cash difference2) Do a different appraisal3) Walk away4) Seller reduces price to appraisal amount (sometimes the seller will but not always)

You should be able to take usual and customary deductions to reduce your tax exposure and still use much of the income you receive  for a loan.

However, keeping in mind the sellers "income potential" rationale, and the fact that the price hasn't been reduced since listing, my buyers agent has suggested to not go below a $120k offer. 

Something you may want to consider is hiring an attorney to reduce your property taxes.

If at the end of the time I have not been able to bring a cash buyer we can either part ways as friends or look at reducing the price.  )Understand they when wholesaling you really can only sell to a cash buyer, your not truly looking for home owners who will live in the home as they will most likely us bank financing.  

This should take away high insurance costs and reduce workers needed for the businesses.First year in the R.E.  

It slightly reduces your cash out, but you don't have to come up with any out-of-pocket money for the close.

I have a 740+ FICO, great income with my job (medical field) however with student debt (and some materials paying off for renovations still) i don't have much savings.I was thinking of refinancing into a conventional loan or a 5/1 ARM to save on MIP and interest rate and aggressively save x1 year to then try and purchase another fixer using an FHA loan again (because I can put down less).  

I'm not sure since it just hit the market that the seller will go for such a reduced price.