There is no installment treatment for unrecaptured depreciation. 

Presumably the CPA's advice on taxation of each entity is based on consistent tax treatment were the entities members of this new LLC.That is, if the taxable LLC receives a K-1 from "new" LLC in which business income is reported, the same should apply for the IRA. 

I drive by monthly and do a visual inspection to make sure the grass is mowed and there are no cars parked on the lawn, etc.

The treatments can help keep roots out of a pipe, but if they are already in and clogging the pipe, the only way to remove them is to snake with a root cutting auger.

I am wondering the type of tax treatment for vacation rentals such air bnb, vrbo etc.

The new ordinance will enforce going from passing the visual inspection stated now to 12 dust samples testing and that's where the issue is.  

My question is how often does a typical real estate investor use some kind of software like photoshop or other fancy softwares to really visualize the change before they start working on it ?

This generally does not make a lot of sense to do.Bottom line is that a SDIRA works exactly like any other IRA when it comes to tax treatment, timelines, etc.  

Roads cost $, waste water treatment cost's $, drinking water, parks, sidewalks, street lights/signs, on and on the list is VERY long of the services NEEDED to support population and, at BIG population, those expenses get BIG. 

Yes if he would be involved in the management in the LLC, then I agree with your treatment.