How can I best prepare for managing two rental properties, including handling maintenance, vacancies, and tenants?

We as tenants had to acquire a shop vac and clean it ourselves, including dragging rugs full of filth and animal hair to the dumpsters.

I am admittedly a newb in the process of getting all of this set up for my first rental (so correct me if I'm wrong) as well but I have some IL-specific perspective to offer: From what I have read, as of 1 Jan 2024 in IL, landlords cannot exclusively accept EFT payment of rents (includes Venmo, Zelle, etc.) for leases starting on or after that date.

I've used mine multiple times in the past deals, including a VA jumbo loan. 

One of my clients found success by including a small home office setup since many military personnel work remotely during transitions.4.

Make sure the units are fully furnished with all the basics, and consider including utilities, Wi-Fi, and flexible leases to make them more appealing.

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

My professional journey includes stints at Equity Residential, Cushman & Wakefield, and now EquityMultiple, where I help investors navigate the world of real estate syndications.TL;DR: Currently located in NYC, Landlady, licensed real estate agent (MA & NY), property manager, EquityMultiple maven, article-writing enthusiast, and devoted real estate lover.

This property would have multiple income streams, including as an airbnb, wedding venue, bed and breakfast, corporate retreat. 

I don't understand how you can't track them down.You could stop paying HOA dues, and that will force them to contact you.As for the PM, I would instruct them to hold off on painting until the termite issue is resolved, which includes providing you with contact information of the HOA board.