Property also includes a covered/RV hookup spot, a large metal shop building and a car port/garage next to the double wide. 

If you hire a contractor who is bonded and insured through a policy issued by a local insurance agency, what is covered?.....

Those are the loan types that cover multiple properties with one loan.  

Rent doesn't appear to cover expenses.

I have fair rental value coverage in my insurance policy, but I don't know if it will apply since the tree didn't fall on a covered structure.  

The rents barely cover mortgage and expenses currently.So, my ask:  What would you recommend doing with the above (do you even think its doable) to both provide income to live on and long term investment?  

What I've learned with handymen and contractors and such is that they are very task-oriented, rather than big picture oriented.

Your Financial Goals are as simple as generating two very basic sets of number...dollars really:1)  Make enough Profit (lump sum returns) to Pay Off your personal debt...ALL of it.2)  Get enough CashFlow to "cover" your monthly bills...ALL of them...and to replace your current method of doing so.The overall Plan, is comprised of a series of Measureable Milestones made up of groups  of the individual Financial Goals (Debt Payoff, Cash Flow)...all lined up in a row.  

Ill send more pictures of outside when i get them.

I would additionally have enough to cover 6 months of mortgage payments (including tax and insurance).