I can understand ignoring the kids to make sure you air on the side of caution but where should the breaking point be? 

As it's a townhome, and the HOA covers most big-ticket items except water heater and air conditioning, would it be necessary to still budget out $100-$150 for both repairs and capex each month?

Prolonged vacancies on rentals kill numbers a lot more than a $50 reduction in your desired rent price to get it filled sooner.

Tankless water heater (2016), central air system (2017), Furnace (2018), New windows installed (2018).

Tankless water heater (2016), central air system (2017), Furnace (2018), New windows installed (2018).

For the time being this home is off the table as we may move back here after my Air Force contract is up.Home 2: We own this home outright and the details can be found on my profile.

I suspect your condensation problem relates to heat escaping through the old roof and meeting the cold air. 

After graduating from the University of Delaware this past spring, I moved 20 minutes back to Wilmington, DE where I work full-time as an Aircraft Mechanic in the DE Air National Guard. 

I would like to own a chain of tiny house cottages/villages across the country for air Bnb or rent or own in some of the nicest places. 

My associate owns a rental property in Texas that is a SFH 4 bed 2 bath and rents out 2 of the rooms to long-term tenants while reserving the other 2 rooms for short-term Air BnB guests.