again, it's not "my" specific scenario. every year, OK gets hammered with storms and people's roofs get replaced that doesn't harm one's premium. my roofer was "able" to tie it to whatever storm they had on this fancy weather app they use and used it to submit the claim. was it really "that" storm?

You'll see some familiar names thrown around a lot: Stessa, Apartments.com, RentRedi, TenantCloud, Innago, RentManager, Avail, Rentec Direct, Doorloop, etc.I think you should search for each app online and see what they offer, how much they charge, etc.

I've started using Rental Hero to track my income and expenses for each of my rentals and flips and I really like how easy it is and that I can upload my receipts straight on their app to keep track.

To that point - does any of the software have an app that accompanies it? 

app=desktop&v=Q2FzZSBD5LE

Your only hope to keep organized with a password app that is secure.  

I am using an app for wholesale listings in my area but even those won't cash flow as buy/hold (it is more for fix/flip).

I have a couple properties and use Stessa as my property management app but they don’t yet have maintenance and issue tracking.

My equity and cash flow crew tremendously larger than the cash app buried, but burying too much of your working capital is definitely something to avoid if possible. 

If you go to the "Meetup" app put in multifamily and location it will pull up meetups for your area of preference.