I have heard that the planning department in the City of Ottawa is a huge pain to deal with, but the committee of adjustment does allow things to go quicker.

Or some other less painful method? 

Are you sharp enough or experienced enough to play with $25K that is not your money?

What is your biggest pain point with Excel?

The GC is hiring a sub that does not know what they are doing, I have had that situation before, it wasn't pleasant so I feel your pain.

I know your pain.

The third option is to sell and pay a boatload in taxes, which will reduce the amount of money you have to play with in addition to writing some painful checks to the IRS and FTB.I've been in your situation and done some commercial RE and oil investing out of state through syndications. 

Originally posted by @David Faulkner:I for one prefer to seek out the exceptions (left coastal as opposed to your tweener coast lake or river) and accept the long term maintenance and upgrades in return for the sustainable appreciation rather than the transactional drag and hassle of dancing in and out of "inventory" every 8-12 years or less (if you're J.) like you're running some sort of used car lot ... please tell me how that is sub-optimal :)The biggest risk I see in high-priced places like California is the three-standard deviation type events that can cause great investment pains. 

As I work in the backyard I find glass, sharp metal, and other garbage that could be dangerous if stepped on.

It's highly unlikely that he will ever sue anyone, because lawsuits are painful for everyone involved, including the tenant.