This is a moot point though since presumably if you could make the same income from a more expensive (ie nicer) property you would naturally choose that asset over the other anyways.

Curious what has worked for others (currently I have student loans and due to the nature of my program I can’t work.

Have you experienced anything of this nature and how did you resolve it?

Does "like-kind" only restrict the nature of the property or also the value?

Naturally, it would be wholesalers, and I`m open to be their friend and client.

In their denial letter, the SBA stated that the business activity of the investment group is not eligible, that EIDL assistance is available only to a small business engaged in an eligible business activity, and that business activity here means the nature of the business conducted by the applicant.We are a privately held real estate investment firm. 

When I was in my 20's (sounds like an old person) I spent my money on cars, motorcycles, bicycles, hobbies, things of that nature, and didn't care about investing.

It does not reflect the taxable nature of that distribution (generally).

Prudence is one of the 4 natural virtues, according to Aristotle.

Of course, I would make sure it fits in architecturally and looks like a natural continuation of my house.