The LLC helps alleviate this.

It could alleviate some/most concerns that sellers tend to have regarding FHA loans, especially the 203k. 

It helps alleviate the anger of the seller over time, after it doesn't sell.

All can be alleviated, at least somewhat by having a nice cushion in.

Ps: Also look into hiring a property manager so you can alleviate that headache and focus on that next investment.

One of the things that could help alleviate some of the problems for single people, seniors, etc. are ADUs and they make it so difficult. 

However I do want to do my best to alleviate his concerns. 

@Chris Springer While you might be alleviating some tax liability somehow (although I'd imagine a city signing off on this would only do so with a tax reassessment which would defeat the purpose) I would say that the appraised VALUE would be much less as one duplex as opposed to two SFRs in the majority of scenarios.  

That alleviated my concern about a failing unit while protecting my wallet from an unnecessary capital expenditure. 

Second, your solution, namely, Section 8 or rental assistance, is one of the best ways to alleviate homelessness, and does so far better than rent control over time because it addresses the legit. needs of both sides.