If you work through all that, then a portion of the rent each month will come from the tenant and a portion will come from the housing authority.  

Your principal and interest portion of your payment will stay the same....however your taxes and insurance can go up (and though less common, can go down too). 

My question is, we received the documents to sign, a portion is pasted below about commission.

Also, don't think of sec8 as guaranteed money. many times the voucher only covers a percentage of the total rent so in essence the tenant is still responsible for the other portion. in several ways sec8 is more hands on that other types of rentals.

You have to get permission from the neighbors for roofs to walk on their roofs, you have to tare up some of their roof (a very very small amount but still some), if theres water damage on the sheathing that crosses over the property line do you force your neighbor to fix his portion or do you take the hit and pay the extra when they refuse?

I would sell now and use a portion of the equity to buy a good house hack while you are still in school (definitely don't use a 15 year mortgage) rather than paying for student housing.

I would max out a HELOC against the condo now to have available & convert the down payment portions to mortgage components when you know exactly how much your purchase prices will be.

Most hard money lenders will fund a portion (90% is typical) of the purchase and 100% of the rehab. 

Fresh paint after 5 years, bought a new washer and dryer unit, knocked out a portion of the wall to create a pass through window between kitchen and living area What was the outcome?

A family member is also a real estate agent and would provide me with the 3% commission on the purchase of the new properties, minimizing cash outflow on the new properties.So my high-level thoughts are, I could downsize and buy two properties, which would reduce my monthly living expense by 1) a smaller primary note and 2) income from the MF offsetting a portion of the primary note, and at the same time I would be able to pull the equity I have built up in my current home, plush my current cash on hand, to further invest after the dust settles.