So glad you've already plugged into the Bigger Pockets podcast - that was a huge source of education for me when I first started.If you haven't already, I would recommend finding a real estate agent that you trust (you've already had a few chime in here with recommendations ;), and also start talking to lenders (banks, mortgage brokers, credit unions, etc.)

It does affirm my suspicion that we could possibly eliminate a few potentials on the regional/national level.

Looking to take this to the next level.

., split level, finished basement, 1 acre, roughly valued at $500kLocated in a quiet late 70's neighborhood just outside an expensive urban area.

Do you sell homes, if owner wants to sell, at what point to do call them for approval, what about emergencies,  Make sur eyou have a trust account, so there is no commingling of funds.

Having this level of details is a must for me because the more accurate information I have beforehand, then the easier the decision is with buying a place. 

Careful you might find it addicting.Bill Chase of Chase and ChaseJeff Charlow of Master Title and EscrowMichael Gross in Bethesda MDAnthony Onwuanibe of Golden Trust Title.

My experience with appraisers has led me to trust my own numbers over theirs.

It is formed at the state level and by having one, you can do business in that state through an entity.  

I think if you interview a few Property Management companies you may find one that you both like and can trust with your cabin...and hopefully they'll be affordable and attentive enough to make you feel better about letting someone else handle your family cabin.