If it's to hold long term, you need to find out the value of the drive thru.If it was me, I would give them a break on rent for square foot added, but increase based on what market charges for additional rent.Good luckGino

By the time I am sick of self management, the offseason comes and I get a break.

Good to have you back after such a long break.  

In that moment, I knew I had to do something to break free from the 9-to-5 cycle that was suffocating us both.

If it is brownfield and you're going to clean it up, they might talk.If it is just kind of a run of the mill deal, I don't think you get any break on taxes. 

There's tons of different ways this can go.... if he is someone that doesn't NEED the passive income, I would recommend multi-fam property w/ 25% down in a strong B or better neighborhood where he can at least break even and focus on a market with strong appreciation and rent growth. overtime, his cash flow will increase, and his net worth on paper will grow significantly. 

If you put a ton of debt on that same property you might break even or actually start losing money every month. 

My goal is more for passive income/break even along with wealth later in life, currently 35 YO.

I want to break into investing via private equity because loans with interest/origination fees aren't allowed in my religion.

Plus, it takes several years to break even on the closing cost and first few years of payments are mainly applied toward the interest and less to the principal.