If the tenant is more likely to take care of the property and continue leasing from me because of a relationship established at the beginning, I would do so on as many properties as possible.

If the property has several units with pet fees and you will continue to allow pets then including pet fee income seems right.

They are local to the area (the first family is moving back to the area to be near family but say they are going to continue to commute to their current jobs which are at least a hours drive from here). 

Lastly, there is a loft style space above the garage that could accommodate a studio (no bathroom however).

If they have permission from the previous owner, no adverse possession.Its continuous for the required period. 

It wasn't a bad experience, but since neither of us were ready or wanting to go down that path at that time we did not continue with it. 

You can add to your portfolio of proven winners and continue to expand your existing business. 

While yeah, each day on market, interest continues to accumulate (assuming there is still a loan) and/or maintenance costs accrue, taxes become due, HOA's may become due, etc. but, at least in this market, it also appreciates daily by some amount.

The trick is that a lot of them (like the Weichert office I initially went to work for when I got licensed) tell a great story about "continuous, ongoing training", but fail to deliver.Best bet in my opinion is to talk with another agent who got great start-up help and sign on there.

Rent seems to continue to go up, and my mortgage as the years will go down, equity will be paid down, and the hopes of appreciation is always there but not expected.