Found a deal I should be under contract by this upcoming week but the problem is I really want to put 20 percent down but if I do that will be all my money I live at home with my parents I have a good paying job 4 bills max, should I take that risk or just settle and do the 5% conventional owner occupied loan and still have some money in the bank. 

Got married, bought and sold a salon, quit my job and started a Contracting Company with my wife.

The house needs some exterior work, namely a paint job, a new landing/walkway, have some pipes removed and hidden plus landscaping and tree removal.

Sounds to me like his worries are well-founded unless you can do a better job of selling him on the structure of the deal.

I have a "regular" job, so I licked my wounds & let these 3 properties gain equity- it was literally money in = money out.  

Got married, bought and sold a salon, quit my job and started a Contracting Company with my wife.

As you change jobs again, you will have access to another chunk from this current 401k and could then evaluate a self-directed IRA.

So currently i have a 90K-115k job depending on OT i have 2 rental properties and under contract on my third one.

I'm not sure the final resolution as that isn't my part of the job, but needless to say the municipality is doing this everyday somewhere and they aren't just going around paying the maximum they possibly can.

You have no context of the job, contractor, etc.