Then, she uploads them to a software called Zubtitle ($19/month) that auto subtitles them.

I'm not a landlord but this is just for personal single owner home and my current auto is through GeicoAlso are umbrella policies mostly comprable or I should ask for a declarations page to study them to see what's covered or any specific questions I should ask?

I also don't allow auto booking.

Don't go cheap on either.I'd also want to talk to the septic pumping company the seller used to get a history over the last 5-10 years to see if it's been properly maintained.With recreational watercraft, consider liability insurance for accidents or deaths.The other potential zinger I see is flood insurance.  

Like car accidents etc.

I would love a dashboard that shows me the the main optics I need to run my business that auto-populates from: P&L's, Balance Sheets, Cash Flow Statements, Occupancy reports, Property Management KPI's, key ROI types, IRR/XIRR.Thank you for reading, and please only chime in if you have personal experience as a AM and/or PM. 

Few suggestions for mileage tracking apps I've tried and liked - TripLog, Driversnote, Magical Miles, Autoed, MileWiz, MileME, MileIQ, Everlance. 

You need to be able to create custom expense pools, auto retail calculations, 1099's and 96's, track expenses for gross and triple net leases.

The only real Pro is it will protect your assets if the renters have an accident that exceeeds the insurance policies coverage. 

Mainly accidents, tenant complaints, extra cleaning, etc.