Advice on Truckee CA property:selling options vs hold

[Jason Borgstede]

I hope this is the correct forum to ask this question in. If not then mods can direct me and I will repost.

I bought a home in Truckee, CA in 2000. The home is 3/2, 1280 sqft, 2 car garage, corner lot, 1978 ranch. The home was totally remodeled in 2008 ( new windows, doors, sliding glass doors, deck, wall retexture, tile and wood flooring, carpets in bedrooms, paint, cabinets, bathrooms tiled, shower tiled, new vanities, new kitchen cabinets, granite tile counters, light fixtures, forced air unit installed, new appliances, everything. Also a new roof was installed 2010. I currently have a tenant that has been in the home about a year and a half. I had hoped to see property values come back up while having a renter but with property management ( i live in alaska) I fall short about $150 a month.

I am interested in selling the house and the best time to sell, for this area, is before the fall. However I have a lease until September 30th. I would like to sell the house to fund the start of a business as well as more investing in Alaska.

Does anyone have advice on how to approach the subject with the tenant? My concerns are having to put a contingency on the sale that new owners can't move in until Oct 1, while not scaring a good tenant out and then not having the property sell. I understand I'm looking for a fail safe plan when there rarely is one but I'm hoping that the experience of BP'ers might enlighten me.

Also, I am not totally opposed to trying to keep the property but even with raising the rent (hoping that wont drive out the tenant) I am looking to break even each month and that's if nothing goes wrong with a 36 year old house.

I'm sorry this is long winded, I just wanted to cover as many bases as I could think of, though im sure i missed a ton.

Thanks for reading.