Chipping away at the debt and getting married seems like the most logical path.

I think th OPs response to this was also a little aggressive with youthful chip fully displayed on sleeve, however, chewing the meat and spitting out the bones, there's some good actionable advice here.There's an old saying that if a man is hungry and you give him a fish you've fed him for a day.

All that does is add to the amount of chips in different piles, add to the amount of chips you need to recover before you can start winning (making a profit), and will leave you less money (chips) to work with to recover those lost chips (cash). 

You think chipping paint on the interior and exterior of a home built before 1978 is no big deal and you will sand it down and repaint it6.

The neighborhood and property were great and rent was reasonable and so my roommates and I all chipped in for a fridge without much grumbling. 

Chip, are you looking to sell a property you own?  

Intel is investing $20 billion in in licking county to build chip manufacturing plants, which is projected to create 30,000 new jobs.

I have had to repair/fix items like chipped paint, missing handrails, lack of insulation and many other items when getting an FHA loan. 

In dressing millstones, the metal tools used, caused chips of metal to embed themselves under the dresser's skin.

Also, you could maybe see if any neighboring land parcel owners would chip in for the cost of water being brought to their street.