The stuff they do is easy to automate with software.

Do any of you have virtual numbers or do you find that your PMS software or messaging through Airbnb and other booking platforms are able to fulfill you communication needs while keeping your personal cell information private? 

I like Doc Hub and you get 5 free document signatures a month.Once the lease is signed set them up with software you are going to use.

You can just give that statement and your spreadsheet to your tax preparer.Trying to add your paid expenses to PMC software is almost impossible, as it will misrepresent what the PMC actually did.Another option is to just send the bills to your PMC and ask them to pay from your portfolio balance.

I am currently experiencing a similar challenge to yours and have been developing software designed to assist real estate professionals like ourselves in lead organization and scheduling of showings automatically.

This may sound like a lot of work but again, use software to automateFinal ThoughtsThe STR/MTR space is getting crowded.

But you can still treat it as resulting in Ordinary Income even though it is reported on Schedule E, which lets you properly report in accordance with the tax results it seems you are shooting for under the tax return loophole.If your CPA is looking at switching it between schedules to get that tax result...it sounds like they don't understand the reporting position fully and/or they just don't know how to use their own software to address it.In summary, based on what you are describing for the situation, it should go on Schedule E, with what sounds like the resulting refund of $17k.

I am software engineer by trade, but have always loved and followed real estate.

The real value of buyer agent is actually the negotiation part but in the future that advisor would be replaced by software too….in the age of Wealthfront, this Ai app replacing buyer agent is easy to do.

My immediate question is on changing PM software.