@David Sharp you should connect with a architect prior to just a general contractor.  

We are in the process of securing financing which has been a pain due to our line of work as contract therapists.I am loving learning on this site and through the podcasts that I listen to daily. 

FHA loans are slow and a pain but they are great.  

Keeping track of these things can be such a pain! 

I know there's many angles here I can take but I'd like to know the least painful!

It's painfully obvious he just wants to argue (why?).

Esp. in dollar terms a few mistakes could gut your return so the risk is much higher and the return is often not worth the risk.4) You typically only have so many great loans so putting it on a bunch of $30K properties is typically a much less optimal idea.5) Managing these properties is a huge pain and good luck finding a great property manager who is making only $75 per property per month (at 10%) or less.6) As you mentioned capex can eat you alive.

I found a local person to help with the bookkeeping, which was my pain point.

The product we currently have for insuring vacant properties while we renovate them is great, but the company we have been using is getting PAINFULLY slow at responding to quotes for standard landlord policies. 

You can drop your price, which is painful but the easiest if you're considering timeline.