You likely wouldn't be allowed to operate a timeshare where STRs are prohibited.

. - Short term rental first bucket of distress based on municipalities prohibiting. - One broker is targeting retirement age portfolio owners. - ADU market should be strong for a long time to come.- Use bandit signs for disposition.- One investor said for their property sourcing, they are touching people 80-90 times before they buy. - All lead gen is 90 days out of activity before hits happen.- There are cost segmenting services that let you do cost segmentation for $450.- You can’t monitor what you can’t measure. - Asset management is building client feedback into customization of investment strategy.

If housing prices had been prohibitive back then, I would have found a different opportunity and worked it instead.

An oil tank leak could be prohibitively expensive and possibly not covered all under insurance.Gino

So let’s start with the commonly mistaken notion that it’s “illegal”, or the similarly mistaken notion that when one signs a mortgage, note and or deed of trust one has signed a contract prohibiting then from selling subject property without paying off noteEvery deed of trust or mortgage than contains a “due on sale” clause states that if a transfer of deed occurs and the note is not paid off then that is a violation of the restrictive covenants and the note holder may elect to accelerate the note.  

Now a landlord (and architect), I wouldn't build out the space without the second stair since it really is a safety issue/liability (especially in case of a fire) if anything were to happen.Full excerpt of building code below:According to the Chicago building code on egress requirements, the third story above grade plane within a dwelling unit [which in this case is the duplex-up unit], all the following conditions must be met:1.) the building is equipped throughout with an automatic sprinkler system2.) the floor area of the story does not exceed 1600 sq ft3.) the dwelling unit has an exit that discharges directly to the exterior at the level of exit discharge.Your third story attic space is unlikely to exceed 1600 sq ft, but you'll probably find the sprinkler system to be cost-prohibitive.

That said, we do lending out of our SDIRA and there are some considerations about prohibited transactions and set up (checkbook control or custodian managed, for example) etc. that should be reviewed with a custodian or SDIRA expert.

I am considering an STR in Ormond by The Sea, but the ordinance prohibiting STR's frightens me.

Also, just be aware that, depending on where in Ventura County, the STR regulations can be rather strict.....and STRs are also prohibited in certain areas of the county. 

If a tenant is damaging property or causing a hazardous condition, that would be something you can enforce (I presume your state laws have prohibitions in this regard, or your lease agreement as well).