I got to my current financial success through a series of well thought out endeavors but with a massive sink or swim element as I am often self guided..."

Well, without any kind of significant cash on their end there is going to be a much higher chance of default.

Oklahoma is excellent for flipping, as well as for buying and holding. 

Well, there is this pesky obstacle called budget.

Quote from @Phil Johnson: I currently have a duplex and a single family which are doing well.  

Further, the costs - depending on your margin as well as the time to learn it vs doing it yourself may not be worth it. 

I am a Broker in Madison, WI as well as an appraiser and self manage some rentals. 

Generally, this type of counseling might have a little fee to it but it's well worth it if it protects you (and them). 

I don't know your specific market all that well but have you done some analysis on your ADR during the high season X your high season occupancy rate and determined whether taking lower priced slow season bookings vs letting your property stay vacant during the winter averages out in your favor?

The Kushner's do it this way, as well as President Trump.