I'm originally from San Francisco and ran into the same issue.

So if they had a 25% cap and were at 25%, then you are out of luck.With that aside, you also have to check with building department as sometimes they may not allow permits to be issued for some of these conversions as they do not meet code. 

We have another property with CMHA and havent had any of these issues.

"Just wanted to get your insight as how we can best handle this" ... with the suggestion that THE TWO OF YOU (you and the treasurer) have an issue and will want to work together to resolve it asap.  

The issue I have with the premise is that Zillow and all the aggregate sites would not exist without MLS.

If the SF's homes work out as planned just 10 homes @ $600/mth in month 61 will be producing $6,000/mth cashflow with NO maintenance / landlord issues except evictions if tenant buyers don't pay. 50 homes $30,000/mth.

If not, could risk constructive receipt issues. 

Congratulations on your recent investment.Moving new residents is a perfect opportunity to form rapport and set the stage for how your landlord/tenant relationship will proceed.We love to meet them at the property on or before move-in day to go over a couple critical items:We walk the home together and address any existing cosmetic issues and any open maintenance items.

He’s my first tenant so I have not dealt with this issue yet.

I don't think I've seen a single issue go unresolved.I have been here since 2017 and recently started engaging more as I became a more well rounded professional.