South Pasadena takes enormous pride in its Craftsman houses built in the early 1910's, and loves preservation, not modernization. 

Part of this is ego and the need for self preservation.

In fact, series insulation is preserved only so long as “records maintained for that particular series account for the assets associated with that series separated from the other assets of the company or any other series.”

I believe more than a few tax pros on this forum practice what they preach and invest in RE themselves (myself included).Judging by your description of your current situation and the hypotheticals on your horizon, I would advise you to look for continuous guidance as opposed to a single consultation to clear this one hurdle.This is a growth and preservation of wealth plan.

I bought a historical landmark building, switched some exterior light fixtures, and the preservation people at the building department made me rip them off and replace them.

Preserve the relationship.  

Since you are wanting to preserve some capital, you may see if the owner is up for seller financing.

Focus on wealth preservation more than growth. 2.

Or start with a light rehab BRRRR to try and preserve your capital but you need to really research the strategy on-line here and read. 

Preserve her credit and give you a little break on vacancy costs.