I would only hire out for major work I can't do myself or emergency repairs.I've dealt with older houses before and the house may be fine for occupants but there's still usually lots of things that can be fixed / improved so it seems a house that isn't perfect would give more opportunities for ongoing maintenance of this sort.To me it seems fairly straightforward to meet the time requirements but I think I need to have extensive documentation?

There are security services you could hire- they are expensive.

You can also start by working for a developer, partnering with a developer, or hiring a developer to do a project for you and learn from them .

Only “off” thing that happened was an email to our insurance rep asking to be placed as the first and only mortgagee - which I caught and they quickly apologized for and corrected.

If you haven't hired an attorney I might consider doing so as this situation sounds like it could get ugly. 

@Angel Pengjust hire a property manager

In my opinion, I'd never hire a real estate agent to help me with investments if they don't personally own investments themselves.

I agree, i just hired a property manager for 2 rentals i own and they use buildium.

I started with an existing plan from a builder then hired the draftsman to make requested modifications. 

I noticed it more in areas where I hired a certain kid to install it.