Different lenders can view income in various ways depending on who you speak with.

I view it as a tool in a toolbox to help you "trim the fat" off the bottom of your portfolio, so you can keep growing with new acquisitions. 

Ideally, my dream is to have a condo in my favorite neighborhood of Chicago (Lake View).I'm 24 years old.

That is because they are looking at the long term view. 

Do some smaller dollar private lendingA property is too capital intensive and $20k will not get you very far.You also did not describe what level of risk you want to take, so that is something also to take into consideration when evaluating where to invest.

Ive known Dave for years now, and the one word Id use to describe him is Integrity.

Just $800 today for the dozer totally stepped up the view of this property.  

The IRS views it as taxable income because it’s not being used for the purpose of deferring taxes under the 1031 rules.For example, if you sell a property and only use part of the proceeds for the next investment, the leftover amount (after paying transaction costs, etc.) is taxed.

In general, the higher valuation properties with views or close proximity to water have higher rates of returns.

Only thing I would add here is to take a birds eye view of the area and try to decide if it will gentrify in your favor so the property appreciates at a higher rate than other areas.