A perception of a win-win is possible without sacrificing business objectives.What this looks like practically for us:Protect yourself- #1 (especially in California) make sure to insulate yourself, if things go south. 

I would also suggest the cap above which the tenant pays for a future lease.not necessarily (especially if the house is old/inadequately insulated). good luck trying to cool the place from 80 to 74 when it's still high 90s at night after 100+ day time temps.  

It needs to properly sized for the square foot and the sun load and the amount of insulation in the unit.

If you can get connected with the people that are insulated from these markets you'll be solid.Eventually, we'll return to a place where affordability rises again.

Wanted input on how much might be involved here to remediate, and what range of costs I am looking at, I fully understand that once the drywall is cut open there might be who knows how much damage to the framing, insulation, and whether it is worth it to even get involved with this property.

This insulates the Landlord from rising expenses over the term of the lease.2. 

We had already been planning to do some maintenance and repairs (repave driveway, re-insulate attic, replace two broken faucets, other minor items), but were wondering if, for tax reasons, we are better off waiting until we close on the new home and this is no longer our primary.Can this work count toward tax deductions as preparatory work on rental property, even if it's currently our primary?

A properly installed electrical system should last a very long time, ive seen homes that still have knob and tube wiring (0 insulation) that still have functioning electrical systems.

Should I just increase my umbrella coverage limits or try to insulate my self also with an LLC?

They come with fantastic insulation between the floors, extra parking on the side with a separate entrance, their own laundry, and plenty of bedrooms up & down.