@Cole HarrisKeep in mind that square footage has a lot to do with pricing as much as bedroom count and/or revenue. 

When I sell it I will be back at square one, no harm no foul.And I do mean WHEN I sell it. 

Mortgage surveys have a margin of error of up to a foot if I recall.

But I appreciate that those who have found their footing in real estate and are doing it successfully want us newbies to understand it takes work and at least some capital.

I see it from a guest's POV if they booked a place and show up to something that looks shabby, then instantly you are starting off on the wrong foot.

I just had a vacancy come up in the middle of a fourplex escrow and the seller had the unit re-rented in under a week for $50/more per month. 6) Yes it's hot, but with individual metering the landlord doesn't foot the electric bill 7) Yes the market is competitive here, but mostly for 3/4 unit properties.

The reason I am asking is, should I list now, there may not be enough foot fall to view the property, not many people move during cold season?

Kudos you've saved and put yourself in a good position to start out on the right foot by house-hacking.  5 years ago my wife and I bought our first and now we have 9 units and have really scaled our passive income stream through those rentals. 

They will most likely be able to give you a rough cost per square foot.

Property Owner, you have an extra 1000 square feet with enough setback to add a 500 sqft ADU on this lot.