if your brand new using a trusted agent in my mind is the way to go.off market properties are full of wholesalers who have zero fiduciary to you.. most will puff ARV and rehab estimates are WAAAY off to make the deal look good.. they will not give you a property disclosure form that the seller needs to fill out etc etc. 

My plan so far has been long term rentals, but, recently, the idea of short term rentals crossed my mind. I

I think a daily allocation of 15-30 minutes for thoughtful communication on top of automations is probably a good starting point.An example that comes to mind is modifying an automated message going out for something personal that the guest shared with you in their communication so it has a warmer touch but the bulk of the lifting is still the base guest messaging.

Everything going through my mind is around securing our income during retirement and leaving some sort of inheritance to my children. 

Starting with depreciation in mind is just wrong, IMHO.Now, stepping down from my soap box...

Mindy

We've found it has superior reporting features, integration features, and is overall more efficient to work within than other REI-specific software.The downside is QBO is not set up for REI so you'll need to do that or work with an expert to ensure it is set up for your business appropriately.Something else to keep in mind is your entity structure and how your entities file tax returns.

First thing that came to mind is: given portion of lot is owned by "community" if HOA decides to move forward with $6k charge shouldn't that be dispersed across the community as opposed to just me?

With that all in mind I cant speak to anything that happened in the past.

Sometimes I wonder if a couple of the folks that @Mindy Jensen and @Noah Bacon have banhammered from BiggerPockets have migrated there.