@Ashley Pimsner, We run into this occasionally. 

Now, as long as I check in occasionally to make sure expenses are going in the right category, I can easily total up certain types of expenses.

Occasionally..... we FB the owner.

There are occasional exceptions to this but not many.

I guess it can happen but as real estate goes I think this is by far the hardest thing to put together sustain and be profitable at.. other than a side hustle make some money occasionally if you darn lucky type thing.. folks I know that do this successfully spend probably 100 to 200k Minimum a year in mailers ALONE  and they have teams that door knock that get paid and Very robust back end systems.. etc etc.. this is a capital intensive business to do right.. 

Heck,  my friends were always hanging-out but i was able to hang out occasionally because i Had to work. 

I occasionally get Springfield leads.

My interests are single family and multi family rentals and I’m considering flipping occasionally for that shot of cash when needed.

Occasionally you will need a new bathroom and/or kitchen so you will need to be setting some aside for that.You mentioned good HOA management.

Apart from your suggestion, I'm not sure there is any good way around that until I have a solid contact in most of the regions.I should also add that while there is occasionally a delicate balance that has to happen to avoid a conflict of interest, I prefer the listing broker/agent because they have the most information and are only 1 step removed from the seller.