Proven Track Record – Experience in vacation rentals matters.

While fees are pretty similar between custodians, read the fee schedules carefully as there are sometimes others fees charged that aren't readily discernible.Good luck and happy holidays!

Does anybody here recommend any mentors/resources/tools/or has experience doing it themselves and would be open to connecting? 

You will learn the most from first-hand experience.

And I feel the ideal portfolio can benefit from the diversification of both.1) Holdfolio isn't a match for me, personally (due to not enough experience, skin in the game, etc).

In efforts to get more experience with IOS, we are seeking a financial partner that potentially has experience with this asset class. 

I laughed when I read that you added value through "Pain", which I assume you meant, Paint ;-)This shows that you are going to hold this investment.

I've spent a good deal of an hour clicking around in circles on the DHA webpage and setting up a profile with their bob.ai platform but cannot seem to get real answers or the ability to speak to someone about the details.Anyone have experience with voucher program as a land lord?

LOL  a softer way to say this is if your simply looking to become a landlord this is a very easy subject to read up on and learn and understand U do not need to pay someone to teach it to you. 

A lot of it is the standard Buildium application, most of the extras I put in there after reading Landlording on Autopilot by Mike Butler.Application fee needs to cover all your screening costs.