This would be a small scale project, a few hundred to a few thousand

Say 220 was roofing ststems for expenses, 221 could be felt, 222, shingles, 223, hardware (nails, screws, trim, drip trim, vents, sofit) 224, decking/lumber, 225, roll roofing (including rubber systems) 226, glue/adhesives...you get the idea.If you are knocking out say 4 basic floor plans, different elevation but all the same materials/grades, you are buying bulk and allocating costs based on the plans per plan.

Higher standard: I know real estate agents are thought to be held to a higher standard, but it's hard for me to envision a licensee that just because he took a basic principals course and passed a grade level exam would be held to a higher standard than an investor that has done several hundred flips or a real estate attorney with 25 years experience.Assuming a re licensee was NOT acting in the capacity of the license, but simply as a principal, does anybody really think a judge would hold a re agent to a higher standard than any other equally (or more) experienced real estate professional, under the same circumstances?

If spending a few hundred a month gets you a complete solution that scales, versus a sketchy cheapie or freebie that will have you squandering your time filling holes, by all means spend the money.  

I feel like for this to be profitable, it'd have to be heavily scaled.    

Finding a GOOD PM, once scaled up, can be challenging.

On the larger number of units does the ratio decrease due to the scaling effect the per unit is less.  

I second what Bettina said: TRY APPLIANCE REPAIR PAINT It is not a contractor grade fix or a forever fix but I have some small patches that have lasted many years.

I am always looking for ways to systematize and scale our business.

I should also mention that my biggest concern is water entry into the space since the soil removal to 16 inches below the joists would also place the crawl grade below the grade of the yard by about a foot.