RE Car: Yes, you should sell your Outback. Push a couple thousand toward it's loan to get it out from
underwater, and then sell that mofo. Pay
cash for a 'better' car,
if you need a car.... Maybe a Honda Fit?
http://boston.craigslist.org/search/cto?sort=rel&query=honda+fitThat's if you really, really
need a car. Good questions to ask:
Can I get to work without a car? (Bike, Bus)
Does anyone else rely on me having a car? (Mom? GF?)
Can we use GF's car only instead/for all car dependent errands? (If she's cool with it...)
Etc..
Possible savings for completely ditching a car: $649/mo, or
$7788 a year.
If invested yearly instead, this becomes...
$122,386 after 10 years.
$482,567 after 25 years.
$968,640 after 35 years.
http://www.bankrate.com/calculators/retirement/roi-calculator.aspxRE: Food and Dining Imo, I would separate these budget items. My grocery spending is usually extremely predictable, but my dining spending is what I struggle to control. Not sure how it is in your situation, but I found that looking at them separately gives me a much better idea of where "food" money is going.
RE: Everything Else I have the same opinion here. Break this down into individual spending bits to see exactly how much you're spending on clothing, car repairs, travel, auto insurance etc... You won't be able to trim fat in categories you don't know you've got fat in.
RE: Tiny House DreamImo this is totally possible, as long as you have a plan of action. For example, we see above that, by itself, not driving can get you 122k over ten years, which should be plenty of money to buy land in a nice inexpensive part of the USA and begin a building project. You just need to pin down a better idea of where you want to build it, what exactly you want to build (how big, made of what?), and who is going to build it (DIY, or pay a builder?). How are you going to make the BNB part of it sustainable, if not profitable?
Once you have that plan, you'll know how much you actually need.
Keep putting money away for this goal and hash out the details in the meantime. Currently your details are controlling your budget, maybe earning more income, dealing with Mom (best to you both), and figuring out if GF is going to be on board (Is she ok with a tiny house? Does she want kids, will they fit in a tiny house? Does she want to be frugal?).
So far, you're on the right track. Good luck!
Ps. If you do become a tiny house builder, I would love to visit your Tiny House B&B. :0 +1 for tiny homes.