I would recommend reaching out to local property managers who specialize in Section 8 Rentals to get a better sense of what timelines are looking like for section 8.

My name is Caden, and I’m the founder of a company building an AI tool to help with tenant management.

Given that the HOA management is the same, any recommendations on whether I should opt for an older 2 bdr vs a 1 bdr in a nicer area?  

Interior and exterior renovations and improved management plan in order to increase rents closer to market and mitigate expenses.

All the above will give you, your management company, and/or your collection attorney some traction if it comes time to attempt to garnish wages or tax returns or levy their bank account.Some of the above may sound a bit draconian, but consider that you may have hundreds of thousands of dollars tied up in a property you're turning over for their unsupervised occupancy, and that they can do huge damage to the property in just a few hours.

If you want to be a career landlord, find a landlord attorney who specializes in property management operations.

I'm particularly passionate about off market deals and adding short term rentals to our portfolio. 

I'm a Broker / Realtor & Property Manager in the Metro Detroit market (Michigan) and have connections with lenders, wholesalers...you name it!

My Denver LTR is much more "set and forget" than my STR, which I manage myself.

To maximize cash flow - manage the properties yourself.