Covered California super sucks, private insurance is extremely expensive & CA fines you at end of year for any lapse in coverage.Employees have no idea how lucky they are, especially here in CA.My workers comp and payroll taxes are almost 18%! 

One particular situation with $700k of debt and $2k/month cash flow may be extremely dangerous and another may be low risk. 

Pull the trigger.

No - FHA loans cannot be held in an LLC or it will trigger the "Due on sale" clause.

I would obviously like to not trigger a Due on Sale clause.

Im actually also in your camp but maybe not as extreme.  

My initial hunch is that there may be extremely limited options of what can be built, and a likelihood of nothing being allowed. 

The above issues are extremely common with all properties I buy, but what I buy are pre-existing multifamily with some meat on the bone. 

If you have the cost segregation done by a reputable company then even if you get audited, you'll have proper support to back up your deductions.Now whether it's worth it - A cost segregation study can be extremely beneficial but its a case by case basis that depends on a multitude of factors.

If the software is not simplifying your life or making you more accurate, you shouldn't use it.Software has extremely helpful features like online payments, marketing syndication (click a button,your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.