I am learning a lot from BP on how to set up a property management system to begin learning the proper way to structure a rental property portfolio. 

Ususally we buy, live in them, fix up and move on (never really thinking about being an investor, we just liked doing it).

Well, you and your buddies can load up and come on over for the exercise then.

The project will most likely end up costing us $10-15K more than we originally budgeted, this comes from being new to all this and not knowing near what we know now!

I was told by an associate of mine that they were charged an additional $15,000 at closing due to a "title fee" on top of the ones you listed.

Perhaps you could form an LLC later on down the line to clean up the structure after some time.That way you'll be able to do clean 1031's with your new partner from property 2 --> property 3 ect.....

If the prospect puts up a big wall and is dismissive about their record, that is more of a red flag than the record itself, but if they were straight forward and honest with me, I will know I can trust them.

You can use conventional financing, up to a fourplex, and if you live in one unit you may reduce some of the property tax for the space you live in as it is your primary residence and you can also buy with very little down as opposed to buying it strictly as an investment property.Duplexes are a great option and you generally also always have at least one paying tenant and can be bought similarly.

If you have room put up a projector screen / projector that is opposite the sleeper sofa and hook up the game console to that.  

If you consistently analyze properties, recognizing a good deal will be much easier when it shows up.