Here's what I learned, my biggest gripes house hacking, and what I regret: https://www.biggerpockets.com/forums/922/topics/1133476-hous...

The biggest point I want to make here is that I would not trust someone who is making you pay a 20k fee to invest with them.

Syndications start off with a lot of unspoken ifs… if we can force appreciation, if variable rates don’t go up, if no unexpected surprises as to the estimates we based our proposal on, etc.To me, the biggest flaw in the single point IRR analysis is to ignore the risk of being a passenger on the bus with a syndication in the first place.  

My biggest challenge with this deal was finding the money to complete it, but my wife and I made it work.

My biggest fear or weaknesses will be trusting lenders, trusting Real Estate Agents, and trusting contractors.

I think you're right, the lack of control is probably going to be your biggest emotional hurdle.There may be some middle ground that softens that blow up. 

One of the biggest hurdles right now is getting a deal.

I think that particular hurdle is what is holding me back from a software solution at the moment because it seems like a daunting task. 

The biggest issue is that we already currently own the property and are unsure where to go from here. 

The biggest challenge, more than handling maintenance, is managing tenant relationships and understanding the legal responsibilities.