I will say candidly having done a significant amount of data-driven research of various financial instruments (including RE), that Cash Value life insurance more than holds its own, especially on a risk-adjusted basis. 

I prefer to do it manual actually. 

Additionally, any advice or recommendations on adjusting my approach to marketing or pricing would be greatly appreciated.Thank you in advance for any insights or suggestions you may have. 

I am not saying this the approach that should be used, just saying there are a few levers that can be adjusted depending on what your overall goal and financial situation is.

The roof now has an adjusted tax basis of $400,000 (due to depreciation over the years).

The new appraiser won't make any adjustments so we're calling a new appraiser to get the value of the home up so we can pull some more money out.

Risk adjusted go to $270,000?

He just needs to adjust his price/sqft for doing more than a typical contractor does

A tenant without a Section 8 voucher would have to show 3 x $1,000 or $3,000 for income.I would not adjust my other screening requirements.

So your goal post today needs to actually be adjusted.