3 quality tenants in place paying just shy of fair market value. 1 vacant turnkey unit. 

Your expertise and advice would be incredibly valuable to us.Thank you in advance for any help you can provide.

Due to insurance costs and high property taxes, we were unsuccessful in finding something that cash flows.

They are usually high interest short term loans that will have to be included in your analysis of the property to ensure you're making a good decision. 

I know you are there, but this is a market that is down from its previous highs by a lot.

My wife will materially participate in the business and I'll provide the financial backing.I've talked to a couple local CPAs and done a fair bit of internet searching on legal entity setup for my situation, but haven't been able to get a straight answer.

This is just a baseline and understand the value of good software but do not see us having 50 units in 5 years since we only self-manage. 

By CLTV I mean (1st + 2nd)/Value.

Also they'd preferably also do business in multi family real estate (duplex, four plex.Have you worked with a great Turnkey company that you would highly recommend?

Otherwise, bite the bullet and pay the real players in this area for what they provide (Buildium, Appfolio, RentManager, etc).