Are you local to Richmond? 

Find and attend your local REI groups. 

This deal came through Partner Driven's local network in Windsor, NC.

or it’s better keep as is with small updates doneI'd start by speaking with an architect or local permit expediter, then someone at the City. 

It is just like law firms from NYC have a full team vs local independent lawyers have a one-man army or a very small team.

@Jennie Berger gave you the whole kit & caboodle on Chicago zoning so I don't have a ton to ad, however, I'd highly encourage you to engage an architect like @Samuel Pavlovcik or @Prashanth Mahakali, both are awesome local Chicago resources.

However, my under writing due to the recent rate hikes shows large cash negative after a high LTV refi to extract the equity so I am not currently actively pursuing BRRRRS and I find this is true for many of the local investors that were doing brrrrs a few years ago.  

Go to BUILD YOUR TEAM at the top of the screen and look for local investors or meetups in your area.

Additionally, I'm banking on a future opportunity to refinance.After less than a year, here are a few tips from what I’ve learned:*Hire a local STR expert real estate agent to guide your investment location.

Here in FL in addition to management I also broker for investors, and curate a weekly vetted STR list with local homes.