I wanted to get your opinion on the various property management software / online portals. 

Find a cleaner, use automation software like hospitable/price labs/turnoverbnb. 

Can you take pictures of your receipts and save them in the app / software? 

But if you have commercial type loans, you may not have much of a choice and HELOCs do not count when you are under audit.

Best software to use to determine value and ROI etc. of package of 13 SFHs and some Duplex, Triplexes for sale.  

I'm trying to self manage and was wondering if you all used a property management software to manage the  STR and MTR properties or if you use 2 separate softwares if any?

The majority of taxpayers are required to settle their tax dues by April 18 to avoid penalties and interest accruing on any outstanding amounts after this date.For those residing in Maine and Massachusetts, the deadline is extended to April 19 due to the Patriots’ Day holiday in these states.How to Request an ExtensionIf you find yourself in need of an extension, the IRS provides convenient options to make the process smoother:File Form 4868:Utilize your tax professional, tax software, or the IRS Free File platform on IRS.gov to submit Form 4868.Individual taxpayers, regardless of income, can leverage Free File for an automatic extension request.Electronic Payment Method:Make an electronic payment using Direct Pay, Electronic Federal Tax Payment System, or debit/credit card or digital wallet.When selecting the payment type, indicate it’s for an extension.

Both companies offer trainings and there's many YouTube videos and articles that can help you learn how to use the pricing software.

look up OCR software

It's not common (because audits are rare), but this type of reclassification does happen and is messy when it does.