Since I have to hire GCs to manage my projects I'm already at a disadvantage with repair costs. 

One disadvantage I see is that it may limit my ability to sell the property to an owner occupant if I have a tenant in place so I can understand that aspect, if I am thinking about this correctly.

What are the advantages / disadvantages to this?

*And yes I checked if there aren't any legal privileges for the elderly that will put me at a disadvantage, and found none what so ever. 

I would probably only have him give me the taxes, condo fee and maybe a small reserve for repairs, so what he actually would be giving me will be well below fair market rent.What are the benefits/disadvantages of me buying it in my name alone?

The disadvantage is you lose the personal touch and that can turn some people off.

I see other normal people see them as disadvantage , this is what the crowd thinks ; but I see those as opportunity. 

Each method has advantages and disadvantages, but the more appropriate people for you to talk to  are your 'partner' and an attorney within the jurisdiction of the property.

What are the advantages/disadvantages of each approach?

There definitely are many advantages and a few disadvantages as well but very worthy of further discussion.It's curious to see that both a mortgage and the government run 401k's are designed to keep you from having access to your own equity/money.