The user interface is dated, unintuitive and requires far more clicks to do anything compared to Airbnb, on both the host and guest side. 

Comparing workload, a multi-unit property will still require showings, maintenance etc for multiple units.

The new appraisal just doesn’t make sense, especially when compared to the first one.

To rent the home, I would lose about $2,500 per month (based on comparable rents in my area, property management fees, etc).Both options loose the same amount by roughly 2 years, and by this time, I still will not have built up much more equity in the home to make selling it a break even unless there is price appreciation by then.My dilemma is this: I speculate that my home will not appreciate much in the next 3-5 years due to the rapid pace of development in the surrounding area.In 5-10+ years, maybe, but by then I'll have bled $150,000 - $300,000.I have thought about this a lot and feel that I mar'-too close to the problem to see the best solution.

As you begin your REI journey here is one tip I have for you:Use this website as you are trying to narrow down the places you want to invest in. https://www.areavibes.com/Its awesome because it gives you a "total livability score" & you can compare different zip codes & streets to others. 

Verify employment and call previous landlords to avoid tenants with red flags.Rent Setting: Research comparable rentals in your neighborhood to ensure your rent is competitive.Use Technology: RentRedi is a great choice.

I'd like to know your thoughts/advice on how to compare long-term and mid-term rentals.

Relative AffordabilityDespite recent price increases, Buffalo’s housing market remains more affordable compared to many other U.S. metros.

Having some prior experience with a flip and a BRRRR locally will definitely come in handy.As someone who’s also from the Bay Area and has done rehabs on my long-term rentals, I wanted to share a bit from my own experience.

I'd be happy to get you some rough terms to compare to other options that you have, but I also agree with Jay that you should be wary of just selling and loosing that equity that you've built up in the property.