@Deirdre Lizio thanks for the tips on foreign taxation, however that should not be an issue for us as we are not actually planning to stay in one place but rather be digital nomads.

Digitize physical receipts for easy storage.

The free option is good enough for tracking basic payments and expenses, but paid service makes digital leases and advertising very simple. 

Tourism, remote workers, digital nomads, snowbirds, retirees, near shoring induced economic boom, growing middle class, massive population (growth) and geographical location.

Note I have 8 digits of local RE and my net worth increases over 7 digits per year for at least the last handful of years.  

And I find it funny persons are all too happy to take a 6/7 figure action on "A" persons declaration of comp/what the #'s are but no-way do they trust "A" contractors 3,4,5 digit project numbers, no-way no-how no no no, gotta get 3+ bids right.....

A lot of great options out there for self-managing if you decide to go that route; aside from providing the basics (listing, tenant screening, digital lease creation, rent collection, and maintenance tracking) some services also offer your tenants additional capabilities which makes it an easier sell on your end when getting them to transition over (ie. their ability to report on-time rent payments to the credit bureaus).

Not sure your guest access, but I have keypad entry, I use the last 4 digits of the phone number used when booking.

For a digital-first business, I have been pleasantly surprised with how quickly I can get someone on the phone or my problems solved quickly.Sorry that you had to go through that with them.

Not sure where you are based right now, but we are organizing a monthly meetup (digitally for the moment so you could connect from over the whole world) and there we are discussing a lot of related real estate topics.