I'm based in Chicago and see a lot of real estate transactions through the eyes of my clients.

Property management in Chicago is no joke...I highly advise against getting into it, lol, unless you have some crazy competitive advantage, which maybe sounds like you do.We've got a small brokerage team, most of whom do not transact heavily and do some investing on the side. 

Do not work for them or fall for the $150 ad set up fee Scott will take your money and Shannon Edwards Transaction Coordinator will cover for him both not answering their phones, responding to text, nor refunding me after 1 week of demanding a refund. 

Over the past few months, I’ve been soaking up podcasts and books on short-term rentals, but I still feel like I have a long learning curve ahead of me.

Fully updated systems = lower.No cross-subsidizing between LLCs keeps our books cleaner.5.

I'm just getting into Baselane, but my understanding is they also offer an option to "split transaction amongst properties or units" and have "separate collaborator logins."

It is death by a thousand cuts, and if you do not have realistic expectations, your partner/investor is going to get really frustrated and stressed out when you have spent a giant pile of money before ever collecting a dime of booking revenue. 

For resources, you'll want to listen to RE podcasts such as BP and any local ones, read books such as rental property investing by Brandon Turner, and set for life by Scott trench.I'd also look to attend local investing meetups and learn as much as possible and network with other investors, real estate agents, and lenders 

I do think this mindset is a reflection of the listing agent in the transaction at times. 

I have an attorney handling the transaction.