The mother would move him out of the way and we would (awkwardly) move on.Until we approached HIS bedroom.

The extra garage wasn't used by the previous owners and is kind of awkward to access as it's behind the house and down under the main floor.

Would there any bump in rent or is just going to be a cost of modernizing an old awkward spot if we do it?

You may be able to find something in the high one 100s, but at that price point I see a lot of awkwardly laid-out units with mediocre tenants at best.

@Narinder Gill I have no experience with it but it seems I’m in the same situation right now.

For a two-family it could get sort of awkward.

Early to mid-December is just an awkward timeframe and I feel you run the risk of not getting your unit rented until after Christmas/New Years and the possibility of it dragging on in the winter.

Maybe it was the fact that those awkward legal-sized pages overflowed with official seals, government certifications, and a liberal amount of scary legal jargon that got me nervous and clearly meant if I ever got behind, I could almost certainly count on finding myself locked in some kind of mortgage prison they send real estate investors to who don’t make payments on time.

Pitch videos for television shows are all the rage these days as a way of getting your personality across before the inevitable awkward Zoom meeting. 

Also many agents prefer to deal with another agent instead of an unrepresented buyer that they don’t know, for various reasons but mainly because buyers without agents tend to require a lot of hand holding and it puts the agent in an awkward spot seeing as their fiduciary duty is to their client, the seller.