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?

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.

., That is a good idea, but unfortunately this airport is not like that, small town = one runway. not a whole lot of big industries in the area ( only a couple). my rentals are Student and full year round tenants, no Air bnb type rentals. i did actually aggressively looked into purchasing a B&B that was for sale a few years ago, but backed out of it, area does not attract enough people to warrant it. i am trying to start something that may bring people to the town, my recent thought this week was actually utilizing the airport with a helicopter site seeing/ hunting transport - currently looking into it, of course that would mean building a helicopter pad, this airport has the room bus does not even have that. thank you for that suggestion though, if i do the helicopter, that may be a service to add to it.