I will probably hire out more work to a contractor next time.

I will say - if you go for the value-add route on a single family home or duplex, be wary of repairs that you can do yourself vs what you have to hire out.

One of the best ways to get involved in this arena is to hire a paid coach.

Are you able to do renovations yourself or are you going to hire this work out?

If there are qualified to do the work, hire them...they will need to pull permits for some work, and likely sub out skilled trades like plumbing, HVAC and electric...work on a draw schedule...only pay for work completed once it's verified...and have an agreement in place before you start any work.

With how long they lived there and their age, I would ask them if they have family to help them move their treasures, and if not, you hire insured professionals to do it. 

Would you consider hiring someone to manage the guest house for you so you could have more free time to do other things?

If you just hire the cheapest or first PMC you speak with and it turns into a bad experience, please don’t assume ALL PMC’s are bad and start trashing PMC’s in general.

Since I work with realtors so much, I bet I could do the listing myself, but still will probably hire a listing agent. 

Then just hire a crew to maintain it.