Stamford express train is 52 minutes by itself to Grand Central...so factor in time to the station and time from GCS to where ever you need to go would probably be 1 hour 20 minutes.  

I plan to use it again for the move-out inspection, my understanding is that the inspection is saved and I can update it at any time and each report is a snapshot of one point in time for the property, so I believe I would be able to just roll over each inspection to the next, does anyone else do that?

Mortgage position is determined by recording date of the mtg........first in time, first in line.

I am interested in becoming a private or hard money lender and in time my desire may grow into becoming involved in the many facets of real estate.

If you want to work for a company that does the things you mentioned then 1) make sure the degree is something that will more likely get you hired and/or paid more and 2) make sure that the benefit is worth the cost in time and money.

Or is this just an industry specific thing that started somewhere back in time and has just been passed down from generations of investors.

My wife does consulting where she will co-host for a percentage of the hosts earnings but we use that money to stockpile furniture for future projects.At this point in time Airbnb is actually keeping people being backed by LLC's/Corporations out of co-hosting by not allowing you to be working under a company so your payout method will go directly to you and not to an LLC.

Don't do this if a slip in time or budget is going to have the whole thing come crashing down around you. 

And I don't think you need any more guesswork.A great PM should know your properties, their neighborhoods, and the markets intimately.

That is both in time and geography.