Let him run this (self-manage) for a year or so and see how everybody feels about it then.How does that sound?

I feel like I'm missing something here, though: if @Joseph Turner gets a cash-flowing turnkey, why couldn't he take out a HELOC to at least partially finance the purchase of the IP, and then pay back the HELOC as the IP cash-flows?

If you can provide them endless value and expect nothing in return, sooner or later the concept of reciprocity will kick in and they will feel a need to help you and mentor you. 

It helped me get the house setup better for both my cleaner and guests.

Feel free to reach out and I can give you some insight on my experience investing here.

 It's understandable to feel conflicted about whether to use a CRM, especially when you already have a PM in place.

But every page I go to I feel like I need 8 different forms.

You don't want your guest putting utilities in their own names because this is one of the items that is part of the litmus test in certain jurisdictions for establishing residency and therefore conveying long term tenant rights.

@Justin Fox feel free to give me a call and I can share with you what I know. 

Always feel free to reach out with any other questions as you get started!