Like you said, the cost should be another goal to tackle not a disadvantage.  

While Hawaii didn't work out, i've since lost 90lbs, converted to Catholicism, found somewhat enjoyable full time employment that lets me put in a generous amount of overtime (Last week I worked 65 hours and on average 55+ hours a week, I haven't had a day off in months), started to tackle overwhelming student loan debt, volunteer, well...you get the idea. 

I flip a lot of houses and have tackled some really bad foundations issues.

The credit card balance might be something he would want to tackle as the interest rate is 19% but again, if he pursues a property it's something he will have to consider as an opportunity cost. 

Tackle this from a different angle. 

So I am looking for recommendations on the best way to tackle the property list.

I don't know if I'd advise you to tackle this one. 

I met the seller who does the occasional flip.... good to keep her number handy in case I am looking for something in the future... and apparently her dad has a small construction company, so thats handy if I need to possibly get a price on some repairs or remodelling that I don't want to tackle myself. 

We've tackled our car and one major loan thus far (approx. $34k), and I've projected that we could pay the remaining $45k by June of 2019 if we keep going at the rate we are now.  

i haven't tackled anything near that scale yet.