Well, have a couple of competitors that are exclusively apartments/dev land for same.Their marketing is targeted at investors along with the mailing list.However, yes, you can get bad/good brokers in the same firm. 

Almost all reputable property management firms have strong indemnification and hold harmless clauses as part of their management agreement.

@Dulce DavisSome private firms would consider blankets but they are gonna cost 2x traditional financingI would take the one with no mortgage and leverage that to buy another and keep doing that - also once in a while may consider selling some inventory to get more cash

The big tach firm's are working on models of other monetization, that's there way forward, how to capture the data and monetize it differently to create relief on reliance of sole monetization from the agent model.

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.. 

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

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.