Thank you, Very odd, Nashville is ranked as one of the best place to invest for short term rental.

Isn’t it odd that the Chicago zoning tool marks this address as RS3?

But I think that if I were in your shoes, oddly enough, what would bug me is that someone else would be handling the tenants. 

For example the rules in Seattle are more restrictive than Washington State overall.

Frequently they can not be modified for use, floor plan or even paint colors.If you get into a position to bid on a historic home let's say, be sure you understand ALL the restrictions you will have to meet.

You know, for those times that we just need a private place to chill or sleep in.We did considered renting in a rent controlled place too but found it too restricting for the kind of "pack and go" lifestyle that we want.

Odds are it would really depend on the bank.

Is there a real need in the community, a needs analysis needs to be done.Will you or can you simply serve an existing non-profit, like Council of the Blind, if so, simply lease to them or individually with a lease guarantee, keep it simple.If I were doing a conversion I would ask P&Z about a R-1 SFD being converted to multi-family, a 5 plex and leave it  at that, P&Z isn't discriminator about who leases, but if there medical  issues or security concerns about a certain population then you may have other ordinances, other restrictions can then be applied.    

If you are wanting to get the best deal possible you may consider @Charles Doehler I have found if you call the listing agent and they can double side the deal you have better odds of getting the best deal.

Why not hire a handyman or odd jobs?