Check with your local PHA to confirm your thoughts as to need, often they will be asked before such a project is approved.

There is a tone after reading the HOA attorney's comments that some power above the power to collect the rent due exists and it does not.

How he reacts and the tone of his voice will give you a feel of how close you are.  

Carbonite is one choice for storing everything and from what i understand is secure, but how often do you need to access that information right away to need the cloud storage ?

So, start with age - how old are things and how likely to need attention?

@Tone Church That's a fantastic idea to have tenants responsible for snow removal and salting and have it written in the lease with the tenants initials next to it.

I have only bought two properties without but both were foreclosure and I knew were going to need a lot of work and anything I found the bank wouldn’t really care about anyways.

How do you think an employer would react if their employees came to them and said, "This pay period, I am going to need half upfront (for hours I haven't worked yet), and then I'll take the remainder when I've worked all my hours." 

You know the relevance, you know they are a necessary evil, but when you do them enough, muscle memory kicks in and it no longer requires active thinking to get you through the process and you can focus on the content rather than the routine of it.

It's been a blast but I did this mostly by muscling through the learning curve (of which I know I still have far to go) and using my savings from my W2 job.