Secured hard money, bought and rehabbed a house, then refi'ed with traditional lending.

When I say this I mean that if you are restricted by capital that keeps you. below the 100k mark then you really don't have much of a choice, however if you have more liquidity that is possible to use then you could go int it with the goal to find something under the 100k mark and still be open to higher priced deals that may have other upside like appreciation and overall area development that increases the price of the home over time- (capitalizing on gains that may not be received by buying in An area that is lower entry but provides great CoC return/ cashflow only as opposed to larger appreciation in addition to okay cash flow.)

@Dana Revallo, as others noted, traditional loan products that will get sold to Fannie or Freddie will use the valuation an appraiser assigns, and that is almost always the sales comparison.  

I agree that it's likely long overdue, it hasn't made sense that loan pricing has been better for second homes than for traditional investment properties.

I would buy the primary traditionally, and feel comfortable covering that expense with your income, and then using the excess cash that you got as a gift, to start your investment career.

However, knowing that he will be financing the deal instead of bringing a cash offer I don’t know how I will be getting my fee at the end of the transaction.This might not be the traditional “wholesalers” situation, but I can use my skills and knowledge to be the middleman and get him a deal for lets say $100k and offer him the contract for $105k.

My issue is more of a DTI problem with traditional lending and a new job.

Had I had traditional financing, I would have not been able to pay the amount I did. 

He moved to FL, and closed the franchise, so now I am back to traditional methods.  

Now, if you can get the interest lower, which in turn would increase the CF, then even better, but if it's a choice between higher interest and higher CF, the choice is 100% of the time the same...higher CF.