Can second home be operated by a management firm that has control over occupancy?

With those stats, you'll pull half the accountants in the forum out of the woodwork, most of us would be more than happy to work with someone in your financial position as it means we can provide a fair amount of value.Whoever you work with, I would recommend you consider finding a firm with substantial experience to offer in both real estate, and estate/gift planning given your goals.. 

a local marketing guru who would frequently meet with us to discuss various business strategies to help grow our detail company heard about the offer. at the time he found out about it the current carwash owners had all but signed an LOI with an out of state private equity firm but were willing to sit down with us and hear our offer!

Just get a firm exit strategy in place (and a backup) for financing before you take action - most cashout refi products have seasoning requirements these days. 

I do have the benefit own owning a IT consulting/software development firm with resources I can leverage.   

For tax planning, I would recommend looking for a firm with EAs or CPAs who specialize in the asset class you are most interested in.

Because now your going to make a list, and 1 by one your going to call every single one of those listing agent's, say you noticed they were listing agent on so-and-so and you'd love to just buy em a coffee if they got just 10 minutes, not an hour, just 5, 10 minutes. 

I’m an architectural designer & drafter who works at a high end firm and we use it for all our remodel projects.

In fact, its so competitive in trying to buy a SFR owner financed note, that most note investors have gravitated to buying non performing, under performing or re performing notes from banking institutions, or the asset disposition firms that represent them.  

Same like AUM too or when realtor says their firm managed 5 billion transaction lol