You will want to have properties under contract before bringing a contractor out to walk the place with you.If I were in your shoes I'd have a 30 minute call/zoom/coffee with a couple of local GC's now and come prepared to explain to them exactly what you are looking to do.For example when I first got started I was targeting single level, 3 bedroom, 2 bathroom, 1,800 square foot homes, with 2 car garages, that were sitting on 7,500 square foot lots, and that were built of block in the 1950s/1960s.

As long as its rational and both parties are level headed im sure you will figure it out. 

That means that not only are they resourceful, their dialogue is effective, informative and useful in you making your decisions.You evidently haven't found someone with the level of expertise you'd prefer. 

That's likely the discrepancy in the data.I have a blog forthcoming for BP which digs into metro area wide data and trends for median price and inventory levels.

Without this workout, the down payment requirements, current levels of interest rates and cost of the transaction would not be incentivizing enough to for investment. 

There are short-term rental management companies that can help with that.One that I work with in Michigan covers the entire state and can advise on local short-term rental regulations or regulations that may be on the way, they can give you an analysis of the demand for short-term rentals in that area, nightly rates in that area, monthly occupancy percentage, and projected monthly income.They also let you choose the level of service you would like from them from full service to minimal.To your success!

@Ben CallahanCheck out markets that can fit with your lifestyle, time, and energy.

The window guideline also has a height restrictions, homes built hillside with a room on the lower level are not always considered bedrooms because if the window is too small for a fireman to get in , in case of a fire it doesn't comply with the guidelines.

As others have mentioned, DSCR loans are generally for turnkey rentals (although outdated rentals may still qualify depending on the level of deferred maintenance). 

The main lesson for us was that there is still a level of due diligence that our team must perform regardless of screening software.