Air might have lower fees to the end user but I just don't get many bookings from them unfortunately.

Sounds Army/Air Force if I’m correct.Well done on your VA strategy.

One major component is how we rank our basic needs (after air, food, water, shelter, etc). 

We drove by the place yesterday, looks like central air might be an issue.

I normally never plan for best case scenarios and always air on the side of conservatism.

List of items to be done - (inspection next weekend)HVACAir Conditioner addition to current forced air furnaceElectricalGarage door motor to 1 car garage door Install recessed lights in living room, and new light fixtures in bedrooms, living rooms, kitchenReplace light switches/outlets to square plastic whiteFlooringRemove carpet, tack boards one main floor and top floorInstall vinyl plank flooring throughout main floor Same baseboardPaintingPaint all wood trim whitePaint kitchen cabinets whitePaint all wallsStructuralRemove half of kitchen wallSliding door for half bath on main floorKitchenReplace kitchen counter top, and match bathroom vanities with sameReplace kitchen sinkReplace appliances with stainless steelBathrooms Replace countertops with same kitchen counter materialGeneral workInstall window blinds on all windows

We would probably be able to finance the initial purchase, but would need to have the two units we are not living in cash flowing ASAP.As far as we can see it will need LBP remediation (in Alabama you can seal it and paint over it) so probably $6k in total for both units to be rented, and an air system in place.

I am committing my self to this job for at least a year so that I don't have to repay a signing bonus but after that I will be up in the air on what to do.

I wouldn’t want this to be an ongoing issue in the future so how do you guys go about handling this with getting penalized with air bnb?

You need to have more than 1 ball in the air because you never know from where you will catch the next break / deal.