I guess my situation is a little unusual - I have a potential tenant who has filled out applications but did not disclose they have an emotional support dog until we mentioned there will be a pet deposit since there will be a dog living on the property as well.

But with the right mindset, strategy, and connections, it can also be incredibly rewarding.I'm glad to hear that you're considering Roanoke Virginia as a potential location for your first investment.

There are two potential violations from the city of Austin.

Look for distressed or undervalued properties with the potential for value appreciation after renovations.

If you're looking for a market with great long-term appreciation potential, Columbus would be worth looking into. 

Are you looking at these properties as long-term investments, or are you considering potential exits in the near term?

So get on Airbnb, where the biggest pool of potential tenants are, furnish your place well and hire a professional photographer and you should be good.

“this implies the property has multiple units (tenants in the back) and the tenants have lived there longer than any potential OO situation (inherited the tenants).  

Our options are buying a new HVAC system, which will run us probably $5-10k based on our research, or we could go with a "rental" HVAC from a local company that includes all repairs, maintenance, filter replacements, etc. for a monthly fee of about $100 over 8 years.I figure we could offset the monthly cost by increasing our asking rent and save our reserves for something else that may come up, but I could also see this limiting our cash flow potential for the next almost decade.Has anyone run into a similar scenario?

So, potentially in theory if you get ahead by one "payment" you are already doing pretty good.You need to be "ahead" on your income/loss, not "behind."