No leaks but I'm sure a house inspector will tell buyers that they will need to replace the roof sooner rather than later.

I need to replace the roof on a few of my rentals. 

Being new and conservative I put in cap ex to replace AC and Water heater within next 3 years ($1500 cap ex, $500 maintenance per year.) 

We have also had to replace both the furnaces, replace some windows, and pay for basic repairs and maintenance items. 

My aspirations in real estate is to promote a comfortable steady income where I'll be able to replace my "JOB" in having more time to enjoy and do more things with my family more consistently.

But until Dodd-Frank is replaced, @Ken Rishel has a great solution - which involves working with the park owners.   

Force-placed insurance, also known as creditor-placed, lender-placed or collateral protection insurance is an insurance policy placed by a lender, bank or loan servicer on a home when the property owners' own insurance is cancelled, has lapsed or is deemed insufficient and the borrower does not secure a replacement policy.

My issue is that I can not perform maintenance on my house (replacing siding and windows, also soil has built up and is touching the bottom layer of my siding).

Depending on the age and condition of the roof we can leverage adjuster relationships and get these replacements bought at a pretty high rate. 

If you're replacing windows, you don't need a permit but if you're putting holes in walls for new windows/doors etc., you need a permit.