My concern, I feel like if I don't make a shift somehow, I will lose potential deals in the future as a result of not getting the needed approvals. 

I’ve done a fair amount of market research, I’d say you have your sights on the right areas.

The 30year term puts the mortgage would put the cost just below 3 units rented but the 20 year is more, I would be losing money until that unit is rented, I fell like ghe 30year lower payment is my margin of safety.

If you think you found a needle in a haystack in terms of a great investment, I would hate for you to lose it over a perceived problem.  

So I'm always nickel and dimed at the end for little items that should have been taken care of during the rehab which is sometimes understandable but the most precious thing I'm losing is time as the contractors have to be scheduled again to come out and then another inspection has to happen. 

I think I could bump the rent on the 3/2 to $1100-1150 without losing the tenant and keep within market range.

Current market value of home: 150,000Current principal balance: 100,000 Are we losing some equity by doing a Cash-Out refinance vs just selling the home?

You should compare any real estate deal's cash on cash ROI to whatever cash flow you would lose from that business. 

@Marc Rice true, what I meant was more that locally if I can get a property stablized with $0 in, I'd more than likely be losing money every month.

you'll have $170K of funds tied up for a few months while you go through the rehab and then refinance. if another deal comes along you could lose out on it if you don't have any cash.