Using this approach enables our clients to get a positive cash flow.

I am wanting to spend the next 1-2 years managing someone's security deposit flow for free in order to learn about the current state of affairs. 

If you jumped into REI and started swimming the only thing stopping you is probably DEAL flow, contractor support, and the economic conditions of your market.

New investor here.Thinking about end to end pipeline management for finding, closing, rehab, rent, hold/sell deals.What tools are you using to keep your information organized, clean, reportable, etc?

The rental property generates approx $5k of positive cash flow per year.

Are you cash flowing the property?

Just be sure to stay cash flow positive and not to give up so much it's no longer worth it for you! 

Today’s investments cash flow around 300.  

You can get great cash-flow (In the right locations), use conventional loans (lower rates), have less to manage, and get in for a lower price.

I would use the flat covering, but have the side by the house raised an inch or so for proper water flow.