I heard a STR focused book keeper say that the her Midwest investors are crushing it, while the more typical markets are struggling. 

Haven't had to worry about this yet but I hear it makes it impossible to evict if you accept even a partial payment so I'm glad I can choose my settings to only accept full payments•I can set up rent disbursements from different properties to go to different bank accounts for bookkeeping purposes that's niceCons•My only big complaint is that I cannot set up a general application link, I have to use the RentRedi portal to send an email to "invite" individuals to apply one-by-one.

They work on our accounting/bookkeeping/reporting/administrative aspects of our rental portfolio.

You have to pay extra for book keeping though, so I made a Baselane account for that which has been nice so far.

@Jonathan Bock My CPA recommended I get a bookkeeper at the end of the 2023 tax season.

Bad things happen more frequently when you buy into the "passive income" idea and don't check in on your properties frequently.Lastly, keep a tight hold on your financials (aka bookkeeping) so you always know the performance of each property.Just my 2 cents.

I understand there is also property management software that combines ACH payment capabilities with feature with basic book keeping features, perhaps work orders/repair requests, document(lease) archives, leasing/listing features? 

Bookkeeping, CPA, 1099 issuance & follow up.

I am an REI bookkeeper, Quickbooks Online Proadvisor as well as an investor myself.  

There's lots of great tax pros here in the forums but you will receive different answers here because they don't have all of the nitty-gritty details of your specific situation and strategy.If you don't have a tax pro you currently work with for tax filing, I can recommend some to you that we recommend through our REI bookkeeping firm.Let me know!