Conflicted

The home we live in now is not ours, we rent. The owner would like us to buy it but we are conflicted. He hasn't told us the asking price but we do know he is a bit upside down in the house which is probably the biggest reason we hesitate to mentally buy this place. I've put a lot of thought into it and here are my pros and cons:

Staying Here:
~No moving expenses
~No moving hassle (isn't that worth like a million bucks?!)
~We feel comfortable here
~We know what we would do to update the home, we've (okay, I've) got it all mapped out in my head.
~Land and space so we aren't crowded.

Moving:
~Land. I'm not sure I want to be responsible for almost 3 acres. And I kind of like living in a neighborhood.
~Less expensive options. Maybe.
~Less updating. Maybe. Although, for some reason, I am usually attracted to the ugliest house on the block and have lots of great ideas. This drives Dylan crazy.
~One level. I've wanted a one level house for a long time. The last three homes we have lived in have been two levels. I would like a spacious rambler.

Something along the lines of this!


Right now we are in a house that looks like this:


The house needs a ton of updates; all new flooring, walls moved, kitchen redone, bathrooms redone, light fixtures redone, exterior lighting installed. I could go on.

I tend to obesses about things. I'm trying not to obsess and trying to allow things to happen as they are meant to.