Even if getting the permits winds up costing $30K, to me... it still seems worth it.Does anyone have any experience with something like this?

@Amanda Lindsay Which property management software did you end up going with and how is your experience?

Additionally, I would like to attempt to do the process Owner/Builder with subcontracting work out as well as doing some of the work I'm comfortable with (I have some experience with bathroom & kitchen remodeling an am not new to the construction industry).

So I am not telling you what do, rather I am just sharing my experience. 

PMC staff are good at maintenance and maybe repairs, but they are NOT licensed contractors with years of real-world experience.

From my experience the first team member to recruit will be a local Project Manager-someone who wants to help you long term as your eyes in the field and boots on the ground. 

Please share your experience!

In my experience that's not actually the case at least in legitimate evictions for non-payment of rent or breach of another part of the lease.  

If you get enough experience doing exactly what you did with your first property there are lenders that would no require your purchase to "season".

Can you please help me understand better what potential concerns in your experience can potentially arise here?