deals are like street cars there is always another one on the next corner. dont get caught up in the shiny object syndrome real estate is not that complicated and PA has some really great areas if your intent is to be a landlord no reason to run all over the country.. 

No system is perfect, so don't waste your time chasing after the next shiny object.

It is currently rented at $1,000/mo, cash flows accordingly with our objectives and I really do enjoy being a landlord and keeping the property well-kept.

It requires agents to offer valuable market insights and investors to be clear about their objectives and financial capabilities, all while adapting to changing market conditions and learning from each other.

If it started with these tenants and you address the occupancy they object to (son), you may still get some petty complaints down the road but the HOA may discount them given your willingness to address what they may see as the big problem (the police call tenant). 

Not because I don't believe in Des Moines, but because many ppl see the bright and shiny object of another city and "the grass is always greener" mentality.That being said, if you absolutely wont invest somewhere more local, maybe because of the economy or the governmental laws in your state, I can attest, Des Moines does have properties that meet many investor's criteria. 

But the potential conversation about the seller's highest objective and the agent's intent is both useful and very ethical.  

From the various responders a start might be:- Welcome - Meeting Objective- Skills/team needed- Flipping Vs Landlording- How/where to find deals- Financing alternatives - Estimating and analyzing deals- Renovation/Contracting- Selling- Property Management - Wrap up/Path ForwardThat should get you started - cross out, add, change, etc. 

My objective is to rent out the home and ADU separately

If they object, they can buy their own property (and wait for their lender to require same).Frankly, in my opinion, this is a peek into the type of tenant they will be - challenging you at every turn.