Beatles, this is my first post on this epic thread. I have to admit that my heart was racing when I read your salary, expenses, and liabilities. Am I correct that your monthly salary after deductions and taxes is 3875 per month excluding rental income (or 4470 including rental income)? On the other hand, your budget already lists 5472 in monthly expenses, and it is far from complete, correct? Where are hair cuts, clothes, kids activities, Christmas and birthday gifts (e.g., motorized jeeps), sporting goods, furniture and decor, car maintenance, house maintenance (all items mentioned in your post)? Even if these expenses only add up to an additional $200 per month, you are currently accumulating debt at about $1200 per month, or $14000 per year. And that is not counting the interest accumulating on that debt, or your other major liabilities. This is probably the worst hair on fire emergency I have seen on this site.
I'm with MMMDonuts on this one. It's not the time to be discussing small labor intensive changes like making your own bread. It's time to sell your rental and pay off a bunch of the debt. Today! I'm a real estate investor and I agree that these people won't care about the roof, they will care about the rental income, which seems good. Just give them a credit for a quoted amount on closing, or list accordingly with a mention of the roof needing repair in the listing. Also mention rental income in the listing. If you go through all the trouble of booking a roof repair for 5k, getting into more debt to accomplish this, do you think you will be able to recoup more than that amount? Not likely.
My suggestions, in order of benefit to effort ratio:
1. List rental with an agent specializing in income properties
2. Pay off HELOC, property taxes, and all high-interest debt to free up some cash flow
3. Contact a CPA and start making a plan for the IRS
3. Keep tracking in Mint and try to reduce your *largest* expenses with the most bang for your buck
4. Come up with a realistic budget that is less than you bring home every month.
5. Don't buy anything that is non-essential, no matter how good of a deal, unless you have saved for it first.
I think number 4 will be very difficult given your salary and expenses, but it is essential otherwise you will just keep moving backwards even if you make significant progress on the other items.