Id have a lawyer on hand, this person seems like they will escalate issues once you notify them you aren't renewing their lease.  

Tell me - someone selling their home to your son, Subject-To - is this a person who has made good life choices? 

I was thinking if I can talk to my neighbor about sharing the cost (I, the landlord, personally provide labor and my neighbor provide material (e.g. fence pickets)).

I borrowed $30k on a personal loan from Discover for 15% with no fees for a plot of land and paid "cash" for it.

You have already admitted that you treat each person differently. 

Every bank at that time had way too many non-performing assets on its books.

With regard to renovations, I always suggest taking incremental steps to bigger renovations or partnering with someone who has already done a renovation at that level.I've been known to just go for the big rehabs for my personal investments here in Chicago , and during that process, it's always more stressful than it needs to be...As far as navigating the competition, I've found the best thing I can do is get EXTREMELY CLEAR  on what I am looking for; then I am confident pulling the trigger quicky. 

Questions they will have is who is the owner, what experience do they have, is their key person insurance against them etc. 

Any insights or personal experiences would be greatly appreciated!

Another benefit is it is much easier to diversify into multiple markets, asset classes and operators.Just wanted to share an alternative - often active investing is the way to go, but it really depends on the person and it is important to know that there are passive ways to accomplish your financial goals.Good luck!