I understand that there are rules regarding prohibited transactions and co mingling funds for Self Directed IRA investments.Here is what I am trying to achieve and would like to know if this is doable?

I did a little research to find out about any specific laws or rules and I didn't find anything prohibiting it here.

Pitches are prohibited, as well as any multi-level marketing, even on a one-on-one basis. 

I am researching on how I can rent out single family houses by the room but it seems like every single HOA rules and regulations prohibits this.

Hi - DSCR Loans do not work for house hacking because they strictly prohibit anyone from living in the property, have to be 100% investment properties only.PS - check out all these helpful BP Articles on everything you need to know on DSCR Loans!

It's better to have them each pay their own, but sometimes prohibitively expensive to update them to separate meters, so in those cases we do what we can to minimize the bills. 

Coincidentally, they also are ESL speakers and I've found that in many respects, more communication is better.My lease has an addendum with several topics: Property maintenance, Yard maintenance, Prohibitions, and Failure To Maintain.  

I bet Michel here would not be able to cite appropriate language prohibiting a licensed broker/agent to conduct open house on behalf of an owner that does not have a listing agreement with anybody else.

Condo rules may prohibit or limit or have additional fees in regards to tenants.

Sounds like he gets wood from somewhere and splits and sells it at the property, and the fresh cut wood implies that it IS the current tenant.Personally, I wouldn't be too bothered by it, if I was able to verify that the operation was legal (no local ordinance prohibiting it, road side stand allowed, and here in Michigan we have bans against moving firewood due to the emerald ash borer, etc), that he was insured against injury, and that my own insurance didn't prohibit the activity.