Because you live with the person versus renting to them in their own individual Unit you may fall under more lenient guidelines in replacing the tenant.

Lots of schedule Es I can not read or understand.I obviously know my rent "income" and my costs (especially since I make NO positive cash flow money on it and mostly loose money (last year I lost "only" -$1175) so i want to know what i made in appreciation versus how much I lost per year for the past 20 years. 

This Corp will get a fee for the management.That would be a way to convert some passive income to active income.As active income does not have the same tax advantages as passive income you need to carefully weight the benefits that you can gain from a Corp (Many more deductions available, retirement plan contribution) versus the additional cost and taxes.

If anyone has any input or advice on whether to invest now versus waiting on the market to hopefully cool off, I would greatly appreciate it.thanks! 

They can adjust the JADU when comparing to an ADU as well but will factor at a percentage for a detached unit versus an attached unit. 

In the residential world, some requirements are relaxed comparing to commercial so it's up to you whether you want to spend the money to have a better planning versus skip the planning and perform the work impromptu.

If you already have sliced up a different way great, use that versus my view below.1.  

@Jesse Kerr the disconnect, in our opinion, is doing everything yourself and keeping it in your head VERSUS a good PMC having to document everything and communicate it effectively to all parties.As the owner, you can make immediate decisions, saving LOTS of time!

I'm not sure what the gift guidelines are for primary versus investment.

She decided to combine two rooms to make a gorgeous master and a "pocket office", versus keeping the 4th bedroom.