Find good training to direct your training dollars to.If you just want to be an agent who is comfortable and fed leads go with a team. 

Between his tips and videos I felt very comfortable with taking the state exam.

I'm very comfortable with booking and advertising on my own but not so with the cleanings in between.

Your intitial post mentions: ""Owes= $24,000 (Charged Off but are accepting payments to principle)"If you can get that debt assigned to you then you are in the driver's seat and you have the right to remove the property from tax foreclosure in order to protect your valid lien, whether either brother likes it or not. 

You have to decide how much leverage and risk you are comfortable with.That being said it is important to purchase your properties correctly.  

My wife quit work 3 years ago when our daughter was born, so the 401k loan was paid off from her job.So we are not taking extravagant vacations, driving BMW's, and living in a 4,000 sqft house, but we are happy and have free time to pick up and go as we please to visit new cities, see extended family, and live by our definition of 'comfortable'.

At that point, if its below, at, or above asking price, then you feel comfortable making an offer. 

Type of property you're comfortable with?  

Is there a way I could get the benefits of having the house, or being able to leverage it, without having to bring a great deal of money to the table in closing costs or additional downpayment that gets her out of home ownership and me into the drivers seat? 

I am comfortable putting in work to gain experience!