Identifying a home on the MLS that already has four established bedrooms is the route that one would take, however, after closing on the deal, additional bedrooms would be added to the property.

Don't give names or addresses, but simply ask hypothetically. 

All of the mechanicals, including permit dates and any identifiers.

Seems to me whatever % you would give up would be offset by simply renting out the upstairs unit.    

In your case, I would simply point out that they forgot to give a value for that space.

I’ve heard from some investors that are perfectly okay with simply breaking even on rental properties in the current market, but I’ve never had the risk tolerance for that.

I've learned over the years that real estate investment is simply a math problem.

If you want to optimize you could identify the busy season and make that STR friendly and then the rest of the year block it for longer stays.

Imagine you bought a property for $2M.The land (excluding any structures) is valued at $400K.Since land is not depreciable in the eyes of the IRS, we subtract the land value from your purchase price to get your depreciable basis.Your depreciable basis is simply where a cost seg engineer starts from when allocating your eligible assets into either 5, 7, or 15 year property.In the scenario above, your starting basis would be $1.6M since your basis = your purchase price - the land value.Having an accurate land value is essential to getting your depreciation/bonus depreciation calculations right.This is the starting point for any cost seg study that you do.

If the inexperienced investor knew how much work, effort, time, analysis, negotiation, organization, capital, and knowledge it takes to successfully find, identify, evaluate, and close on a property that fits the criteria that gurus falsely claim they see 100’s of every day, 99% of them would abandon their real estate dreams” and pursue ostrich farms, mink breeding, or setting up a “down line” to sell condensed cleaning products that their “upline” has an exclusive distributorship on for the southwestern quadrant of Bisbee, Arizona.