If you're subject to the Alternative Minimum Tax (AMT), these deductions may be limited.

If he doesn't qualify, advise her that she has to 'cure' the illegal occupancy immediately or be subject to eviction. 

We would do a Self-Storage location with containers subject to zoning.

When people bring up Subject To (very risky) and private money it's usually because they have seen a lot of scaling content.

Roth IRA contributions can be withdrawn tax-free, but earnings may be subject to income tax and penalties unless the account has been held for five years and you're 59½ or older.Instead, consider rolling over your IRA into a solo 401(k) if you're self-employed, allowing you to borrow up to $50,000 or 50% of the account balance, whichever is lower.

I may explain that while I’d like to buy/finance/invest in his property, I need to earn a certain return on my invested capital for the given amount of risk, and if not able to earn the return on the subject deal than I will on the next deal.  

Look into seller financing or subject to properties in the area that you want to purchase. 

You need to develop a subject matter expertise and treat this like the hands on business that it is. 

My advice is if you cant easily afford it and you have to put it on a CC.. rethink that.. networking is great but there are all sorts of meetups and REIA clubs that are basically free that have speakers come in and talk on all these subjects. 

Even if the property is short, a contract with a buyer, even subject to short sale approval, should work.