He said " he would rather pay $2000 a month than sign a lease with such a crazy price hike "So I have a few options , give 60 days notice , move into the bigger house , now have my larger house, extra bathroom and garage for my hot rod and only increase my portion of mortgage $350 as I believe renting the 1/1 at $1300+ will be cake .Or supply 60 days notice and get new tenant at anywhere from 1850 -2150 a month and stay another year in our small 1/1 . 

Side note: I have realized that a lot of the bigger companies tie you down to almost work full time to make it worth it. 

The walls on both sides of the sink are water damaged, and it looks like a tile is missing on the floor.

I would hire a surveyor, this will prevent any problems down the road, then there is no question where your property is. also check with your town zoning ordinance on fences, you will have to get a permit, the height of the fence is usually regulated and the distance back from the property line you have to install it ( usually around 5" back) posts on your side and the fence facing the neighbors.

If the latter, do you have a contract and did you ever discuss expectations on both sides of the table?

this happens all the time.. the closing attorney who closed your deal without a recorded satisfaction or reconveyance deed what ever Is appropriate there is the one on the hot seat.. 

@Jeffrey Holst yes I'm definitely looking on the smaller side in terms of # of units.

With a hot real estate market and multiple offers on properties, can I change properties if I'm outbid on initial 3 properties?

The market is hot in the Boston area, so capitol is the main issue for me at the moment.

On the conservative side, at least $75/night.