"A bird in the hand is worth two in the bush" as they say.I think ideally it might make sense to have an assistant to call people to let them know of receipt, status and to turn paper around if that's all that needs to happen to maintain professional courtesy.

Ideally I would like to house hack in a triplex or something similar, but my wife and I cannot imagine moving again and we are only in a SFH now.

If you purchase a value add B/C class property, ideally you want it in a A/B area respectively to see the best opportunities to move the value up on that property with renovations.  

If you want to keep them on and can get them to sign a new lease that would be ideal. 

The "ideal" plan will be to get also have them oversee any properties I acquire between now and then.

I spoke with the realtor and he said it's just a difficult house to sell due to the size, which to me seems ideal for a rental.

Ideally 10% CoC return.

Ideally 10% CoC return.

Assuming you are only leaving 5K in equity in a property this would be the ideal scenario. 

Our ideal scenario would be to buy a new house as our primary, live there, rehab, and then start renting it in a year.