If they were insured with Cal Safe they are both dramatically underinsured and a single neighborhood would deplete the programs' reserves. 

The current owner bought it for $30K and I know they had to clean up a lot of title work and started doing repairs. 

(The floors are tile and terrazzo, so it is easy to clean up spilled paint.)We haven't gotten an estimate on the painting from a painter yet. 

One of the pro's is Investors can tap into retirement funds to finance deals without depleting cash reserves.

Bank Statements and Asset Depletion can be used with helocs!

If your manager is just 'keeping an eye' on things, collecting/reminding on a few rents here and there and some light cleanup while being compensated in free or reduced space rent then classifying them as 1099 subcontractor is great. 

Take a look at Personal Property versus Real property coverage, plus clean up costs to make sure your covered.I would also look at covering your project from the Subcontractors. 

There have been a few things that I feel like they could clean up, but it seems like they work hard at updating it to provide a lot of value. 

My question is, would selling this asset now to clean up all my personal debt (~$50k) with the leftover used to reinvest be my best move currently in your opinion?

You may be serviced 3 times during the storm and a final clean up and salting after the storm .