We're working toward financial independence so the question really comes down to increased cash flow vs. decreased liabilities. 

Spending an hour with a CPA who understands your overall financial situations would be time well spent, but there are some general rules of thumb:If you hold the asset for less than one year, your profits are considered short term capital gains - which are taxed as ordinary income at your standard tax bracket rate. 

Children have a responsibility and that responsibility isn't to try and figure out ways around the system when it becomes inconvenient financially.

It sounds like you're already working to put yourself in a better financial position, so even if they don't think they can lend to you now, they would likely be able to share criteria and a timeline for when that would be possible. 

It stands to reason that anytime someone takes a big step forward financially (e.g. a first purchase, a multi-family unit, a first apartment complex), the risk may overcome them.

We have been saving what we can and educating ourselves in order to make the best financial decision but we are torn because...

I think his methodology is as much human nature as it is financial.

A friend is looking for ideas for next deal, here is a financial snapshot - hopefully some of you w experience can give ideas of what you would do in this case.

I fear the financial stress will be great without having anymore additional income than my 8-5 job.

Another area developing rapidly is around Randolph St and Halsted.