The style of the home, the space you are trying to heat, the price point of the property all play a role.

Decide on your learning style such as in a classroom or online. 

The old "octopus" style systems are all garbage, and they have a ton of windows, so energy efficient they are not.

Month to month leases are not short term leases, usually they are 1 year leases that are transitioned into moth to month when the lease term expires thus making this completely different from Air BnB style rentals

In fact Hilton recently announced they are buying the Mandarin Oriental and rebranding it a Waldorf Astoria so that's very telling.  

One other caveat: these are townhome style condos, and are legally described as "building and unit" not "lot and block".

Though it is in good shape, it has an old pre-war "feel" and has not had the usual flip-style renovations that you find on Zillow.My questions:1 - Should the house be priced significantly less than renovated houses of a similar size?

Another way to do it would be to start small, and do it JV-style.

A split level foyer (as much as I hate that style) is almost ideal for this.

You can not afford your present life style.