Based on the list above, are there certain areas/tasks that you would tackle first before others?

Well this comes from the general spamming involved with getting these from leads to contracts.

So you have to ask yourself, are those issues deal breakers or would you be comfortable continuing forward, knowing you will have to tackle them after closing?

If you are going to target mostly off-market the license will just be a cost, and some brokerage you attach to will spam your in-box all day with "You don't wanna miss this" meetings, etc.I think the more consistent and targeted synergy with investing would be General Contractor. 

Also, him and myself do not think we can tackle this big of renovation since the house needs plumbing, electrical, etc.  

I think it’s safe to say though that with the way the foundation repairs have gone, it really won’t have much of an effect on the home shifting and we can now begin to tackle the upstairs units.   

I tried online but that caused me to get spammed with calls.

We talked to one lender about refinancing our other investment property at the same to gain extra cash, but with that lender's higher construction reserve requirements we're still short.Anyone tackled this problem before?

I am also looking for how to tackle a cost effective exterior painting.Even I can help the contractor to do the work if that helps, I just don't want to go through the learning curve of the remaining repairs.Thanks I'm advance.

I was your age when I bought my first property and made some mistakes (some wins too) including not really being prepared for the scope of work I was tackling.