At least you do not have other tenants living next door that are bad apples too.

Tyler, you are talking about two different things here, apples and oranges.

The size changes the materials needed, but the contractor still has to lift the roof, frame the supports, frame the new walls, install windows, new flooring, insulation, sheetrock, etc etc etc.

That sofa is the bed for the tiny apartment - the recliner piece lifts up to hold blankets and pillows and under the seat area is a trundle bed that lifts up to fill in the "L" to make a queen size sleep surface - very comfy - not like a traditional sleeper sofa.

It could very easily have an ARV of over $50,000 so you're really comparing apples to oranges.

If he has crew that will be doing the heavy lifting and he just has to oversee them, then that shouldn't be a problem.

(By the way, I'm guessing your answer is still the same, just be sure to compare apples to apples)

It is not apples to apples, not even close, it usually just gives a rough number based on a per sq ft basis and does not take into account at all anything like a pool, upgrades, etc.

It's important to make sure you are comparing apples to apples when comparing quotes from contractors. 

Also, amenities and condition of updating affect rent more than square footage, in my experience (as you stated, a luxury 1 bedroom might rent for more than a 3 bedroom of the same size, but then you're not comparing apples to apples - if you compare a 1 bed and a 3 bed in the same neighborhood with the same amenities and interior condition and square footage, the 3 bed will command a higher rent).