or it’s better keep as is with small updates doneI'd start by speaking with an architect or local permit expediter, then someone at the City. 

Given all your data on historic pricing, average length of stay, and pricing at the 25th percentile, please let us know if you're able to push up the VRBO chain to speak to a Supervisor (or equivalent) and have them verify the data that supports your position.I can share that calling the VRBO support line: 877-202-4291, identifying yourself & property ID, and requesting a Supervisor politely and repeatedly, can lead to different outcomes.

Shortly after the crash my tenants learned that condo developers were renting out luxury apartments in the area for around the same rents I was charging so I was forced to lower rents. 1200/apt 2 1050/apt3. 

@Brooke Carlton did you speak with the current lender about their willingness to finance some of that gap for a potential buyer? 

I myself have invested in Cleveland so I can speak on that market.

I would like to speak with local investors, real estate agents, property managers, lenders, etc. from the area.

Speaking in generalities of course based on what I usually buy.But, these days I'm trying to be more passive so things like syndications are a more likely path for future investments.

I can speak from experience as a student at Texas A&M, I lived in a 5 br/5 b house and I knew plenty of other students who lived in similar houses or "Ag Shacks" if you will.

I would love to speak with people that have experience in the area.If one of your friends would like to talk to me and share some advices it would be great :) 

Also I have not worked out the financing yet. if I just use my cash then the Cash on Cash drops to 8 or 9% and that would be below my Cash on Cash target.Generally speaking and of course just numbers I picked out of the air for reference when running numbers in my head, I am looking for Cash on Cash greater than 15%, high probability of long term occupancy, and no expected major Capex for 2.5 years after purchase and purchase time repairs which I would add into the cash on cash evaluation before pulling the trigger.So there are some more details to be worked out in my head but being it is my first one and only learning what I could from youtube videos I thought I would get some feedback.With all that said, in my head it seems like it could be a good start.Thanks again Jaycee and Gavin for your feedback.