He is definitely more conservative in his advisement, but seems willing to go along with defensible positions that fall within the tax code.

We do lend in this area but 100% with no reahab seems uncommon.

There doesn't seem to be a lot of MTRs (rooms and entire units) in the area just based on initial searches on Airbnb and Redfin, but I understand this isn't the only indicator of demand.

Most developers, it seems,  share nothing. 

This market has very little supply and seems overpriced in many facets (less than 100 MLS properties), but I'm determined to find a good deal within the next 3 months.Capital is now fully acquired and just looking on ways to find and analyze deals.

They told me they applied and are saying they need a tenancy agreement or lease which doesn't seem accurate.

That may seem obvious but in my experience, 99% of ongoing maintenance issues are because the property is old and needs either a large cash infusion to make them go away or what I like to do is 1031 exchange into something newer that requires less work. 

A lot of people seem to think it can be a side hustle.

Your plan seems viable, but it's advisable to consult with a real estate focused accountant to fully grasp depreciation recapture and the complexities of a 1031 exchange.

From everything I've read something doesn't seem right here.