However, I don't see how I would be able to do that if I am not cash flowing or worse, ending in a deficit.Any perspective, strategy or help with my situation would be greatly appreciated.

I haven't thought of it from that perspective.

I can offer a unique perspective.

Using a turnkey condo for short-term rentals on weekends while reducing your commute could be smart, as long as STR income covers costs and local regulations allow it.From tax perspective, if you personally use the STR as you intend, you cannot create losses under vacation home rules.

Throw in a dose of imposter syndrome and fatalism and you have a recipe for some mood swings right before a property is booked again.From a practical point, I would recommend great photos, a clearly defined target to whom you are advertising and understanding the best pricing of an area really well to ake sure you get booked in a timely fashion.From a more meta perspective, be aware that these listings don't typically get booked well in advance (families displaced by flood or fire, traveling nurses who need a new contract ASAP, and construction projects that realize they need a speciality engineer on-site RIGHT NOW don't book ahead). 

Also, having the perspective and looking back at rent growth and appreciation from your own personal experience rather than reading about it makes you realize this is not as crazy as you thought it is.You have to grow your portfolio wide (units), before you grow it deep (equity).

@Max Bellino,I understand your perspective.

Here's another perspective: Insurance is for liability protection.

If I've said it once, I've said it 1000 times: don't include a clause in your lease if you don't understand it or are unwilling to enforce it.I recommend you politely explain your perspective, then ask her to work with you to help market the property and find a new renter. 

You are a typical internet anonymous troll who pops in and out and sauces the forums with their perspective and looks outward and not inward.