It's always a plus when you can get your property valuation increased and the tenant pays for the new item, just so long as your downside risk is mitigated, too.Good luck!

I didnt see my tax bill showing a line item.

Being so close to the bases, you could make change it at some point from a long-term rental to short-term (for families coming into town) or mid-term (for military contract workers) and that would earn you more.For now, I would keep saving and invest in something else and leave this as it is.

Do you cover items such as lawn maintenance, extermination, alarm and cable services?

He is also a military vet. 

I am retiring from the military soon and am looking to get into commercial real estate.

But I would be missing items necessary for taxes, etc.

COSTS:  I would look at any-and-all things needed to run an STR including items that are often done by owners--for example, property management.  

Hold Harmless & Indemnification clausesAs well as other items.

Highly agree with Nathan - Buildium is a Nightmare to use for STR, it is not appropriate at all and prone to a lot of errors due to the sheer number of manual items that need to be adjusted in there.