A lot of houses have no windows on the South side and that is for a reason.You didn't say where you live but unless it's the far north, I would pick house #1. 200 extra SF is nice too.....If there is not enough sunlight down the road and it bothers you, you can always add a window on the front, or even easier, put in a Solatube in a central location.

My 40 year old lives in house.  

Second, commissions are set at approximately 5-6% because that's what it takes for an agent to earn a living.

I have a 3 party who I have used since day one $45.00 to do background  so far so good couple bumps nothing too big .Last place they lived is BIG make sure you don't skip any thing that should be done .When they are serous take a picture of the DL of all folks on the rental just like a apartment would do .

I've been living in the house with one roommate paying $600 of the mortgage.

They love living there but they want the unit updated, about a $50k cost. 

You live in one of the biggest REI areas of the country, so smart to take advantage, especially now that they opened up 3 and 4 unit multis to owner occupant low downpayment options.I looked at a great 4 -plex available in Gladstone for $365, will probably go for $385.great deal. good condition. $800 per 2 bed /1 bath unit. quick mortgage calculator puts zero% down monthly payment at $3500, plus then offset with $2400 puts you on the hook for $1100. 

Step by step guides, explainer videos, calculators, etc?

One thing I will say is to start before you think you are ready, learning from experience will always be more valuable than any BP post or youtube video that you watch. 

Recently updated with brand new countertops, fresh paint throughout, sleek new flooring, and stylish light fixtures, this home offers a chic and turnkey living experience.