My current primary, which I have been in since last October, is in need of a new roof.

The owner attempted to fix the issue but tore up the drywall and couldn't locate the source of the leak.

If the washer you provide leaks and ruins the tenant's property then you will be responsible to repair or replace their belongings. 

I repaired some interior work costing me about 7k and the roof which is about 18k. 

A roof on a typical duplex may cost $8k to tear off and replace.  

First off, once the work was pretty much done, I found a leak after this crazy storm we had.

I need help deciding if I should keep my primary residence and rent it out or sell it and then move into a new one, I have already done a cash out refi of 60k if we rent it we would get 150-250/ month profit not counting cap ex and if we sold we could get 5k-20k property is worth 250-280 ARV , the property has brand new roof hvac and hardwood floors with in the last year or two we will also be using va loan to buy. ps my wife wants to sell and I want to rent it out 

Even had a brand new roof and young HVAC.

That's where bad experience/nightmare come in.Lastly, to answer your question, to build a basically designed, square/rectangular house without crazy jigsaw puzzled cuts on roof, the following price is a good competitive construction only price for what you need to do:Around $165 per sq ft on conditioned space (for an average 1200 to 1800 sq ft house, 8-9ft high ceiling, everything is investor grade finishes), $90-100 per sq ft for garages/unconditioned storage, $60 per sq ft for porches/opened spaces.  

I had a crazy incident where a huge section of the roof blew off in wind storm in May 2022.