thats basic list one can add.Value add /  New construction / land entitlements/ Timber / Minerals/ Lendingetc etc.. far more ways to actually make money than just buy and wait for rental income to payoff debtl 

She actually told me it was a triplex.

I've got 14yo triplets actually!

The real actual job is still the contractor analysis. 

If you don't actually replace the damaged property, the insurer will normally only pay you the "actual cash value," i.e., the depreciated value of the property.

I’m having a hard time reconciling your title and what you’re actually saying in your post.

I actually decided against investing in Cumberland for the time-being so don't have any tips/advice regarding PMs and such out that way

If not I wouldn't bother selling as there is an incredible amount of money lost in buying and selling properties, so you have to make sure you have a plan to maximize the equity and actually have enough. 

At this point I'm realizing can scale a lot faster with those partnerships, and beginning to try and understand the actual structure of the business behind these kinds of partnerships.

The challenge with property managers is that they are actually very expensive.