I feel the key is to have good relationships with your "boots on ground" building a solid team of cleaners and handyman to help you make it happen!  

Turn-key vs. value-add?

Maybe set up some key word alerts to help you track down those threads and see what others are doing.

Learn the basics of cooking now -- it really is one of the main keys to living cheaply later.

Now that you have the knowledge and presumably some money to work with, the key is to pick one strategy and go all in with it (at least for now).Here's one option for you: You already both have steady paychecks to fund your current lifestyle, so more income is not necessarily the issue right now, first you may want to focus on reducing your expenses.

The key to being a wholesaler or investor is to have exclusivity.

The key is that the tax paying entity for the old property has to be the tax paying entity for the new property.

Being a general contractor and an experienced investor I see stuff from multiple angles and the key component of what you said was he is selling this property in the winter and that's exactly for a reason I've seen this happen many many times.

Would any of you all be able to share some insights on how you came upon a good property manager and what were some of the key questions you asked to make sure they were the right fit? 

There are also some key terms in the leases that are very important to address as well.