So theoretically, you could House-Hack 1 per year, getting a new owner-occupant loan each time.You may hit some limits that would keep you from acquiring 1 per year with conventional financing indefinitely.1.

Most of the landlords I have talked to in the area are long term owners using the rent to pay off the properties and holding them what seems like indefinitely.  

The 1031 defers indefinitely both profit and depreciation recapture. 

And LASTLY - My car is my office,  I am driving around from this property, to that property, etc etc, so I am spending a ton of time in my car, I am sure many of you are also - so yes it does make a difference when you have a new car, you are more comfortable, you work better (again it depends on the person, some people get comfortable and get lazy, some other people driving a new car makes you work harder) the newer technology does make you more productive/efficient, you work better, would you rather spend 4 -5 hours a day in a brand new car or a used car? 

If they don't do what I want them to, then shame on them for not letting me stay here indefinitely.

Unfortunately he has a not so great personality and I couldn’t see myself working with him for an indefinite amount of time.

You could house hack in a nice neighborhood, accept negative cash flow if and only if you could afford to hold as a primary indefinitely and could get some nice forced appreciation. 

Then he can exclude up to $250K ($500K MFJ) from capital gains on the sale of his primary residence.The capital gains tax can be deferred (indefinitely) with a 1031 exchange instead of a sale provided your client wants to continue to own investment real estate.An installment sale will spread the capital gains tax out over several years, reducing the amount of tax paid in a single year.

That will be hard to impossible to sustain physiologically indefinitely.

What parts of Maryland are you interested in? Definitely