If the framers didn't take a lot of care, it's actually easy to have a hump. 

With a little effort you could probably get a win-win on hard to fill hump seasons or a great in-season change of pace

Don't have all the details obviously but I think you should pull the trigger and not stress too much on the closing costs, if you listen to a lot of the podcasts/stories of experienced and successful investors, the advice is almost 100% uniformly to just "jump right in" and get over the hump on the first property, the learning lessons and the push to get you out of the paralysis analysis phase seems to always be well worth it, way more than potentially leaving a few pennies on the table

Sacrifice whatever you need to sacrifice to them to help you get over the hump.

Overkill to me unless the place is pretty thrashed/old/poor work done before etcId consider adding some of the outlets that have the USB plugs for charging phones ets without the adapter etc. 

A friend in the hood had guys humping a trash cans, another drunk ones that cursed them the list goes on and on.

You are essentially asking someone to agree to be in debt with you in an overleveraged position on a home that is not earning any rental income.When we ask a family member to do this it's due to us being family and they are helping me out.  

He could potentially be interested in this and retain some equity in the home and essentially help us acquire it from his brother.How would you see us being able to use this property to springboard future investments? 

I'm here looking to find a friend nothing major just to share a tip or two with maybe that can turn into us being business partners, who knows.

Since we're in different price ranges, I don't see us being competitors.