The number of months depends upon how well (or bad) the management company is running.Type of business for this offer Mom / Pop shopBusiness owner is heavily involvedBusiness is running with a skeleton crewThere is no marketing or sales divisionSystems are not well documented or non-existantNot a lot of add ons (programs / fees)Typically have another career as a real estate agentTypically less than 100 propertiesModel 2 - Revenue (1 - 1.5x)Offer is made based on yearly revenue.

A fitness watch is a good add on to keep you honest.

Quote from @Kodie Talley: Hi Ryan! 

But as Kodie stated, you will need to be cautious on how the offer is written and make sure you did a thorough job of explaining the deal to your hard money lender so they do not back out and you lose your EMD. 

Several of the companies you listed, ex: propstream are great list aggregators, but their add on services (such as skip tracing) can be sub par. 

It needs to be intrinsic for a DSCR loan to qualify, or they penalize you with an excess add on fee and/or rate. .Secondly, an IO really only make sense if you're investing in a short-term duration. 

Do this for the whole house and then add on 20% for complete unknowns.Realize that there is some reason that this owner does not want you to see the inside of the house, and plan accordingly.

There are no add-on fees (you pay the same if you came in cold, or if you got referred), their fees stay the same for everyone no matter what, and they are very honest.  

I would love to find a software to help automate the following tasks, there are lots of options, most at $40/month, would prefer cheaper but will probably pay this for the best software that can best handle:- creating a direct booking website from my Airbnb listing, I know some websites have an auto-builder which would be preferred- handling automated messaging- handling calendar and payments, including add-ons- sending agreements and collecting and returning depositsI am overwhelmed with the options and suffering analysis paralysis. 

Is there a certain level of insurance  (liability only) or add-ons I should concern myself with?