At what point does cash flow outweigh appreciation, if ever?

If you take on your friend as another tenant, it may help outweigh some of the potential cons that would come along with this process.Hopefully an expert in this area will be able to provide a more concrete response, but I unfortunately don't believe it will work out as you have proposed.

Does the income, steady job, and long rental history out weigh the bad credit?

The potential protection from an LLC far outweighs the downside of using one (fees, slightly nuanced tax returns).You might also look into an umbrella insurance policy in case the LLC shell is pierced in a lawsuit. 

Summertime the hard numbers are outweighed by market conditions.

The closing costs would outweigh the monthly savings.

If so, and depending on the cost and complexity, will the benefits outweigh just paying the $800 CA Franchise tax?

So, the fear of never trying simply outweighs the fear of failure.

If you are doing multiple BRRRRs where you cash out 65-75% of a property's equity and create a long-term line of debt, how does the amount of debt you accrue not vastly outweigh the monthly income you bring in?

This gives me a property with a comfortable net cash flow of around 500/mo with the rough estimates, but not enough to outweigh my 900/mo rent.2.)