He calles them "poor people" "economically disadvantaged" He threatened to evict them if they don't rent his appliances like used ceiling fans.

As a wholesaler, hopefully hearing from some of you with experience with these sites, what are the advantages or disadvantages of each of these sites respectively... as far as which search criteria to use on each platform?

When January comes, you will have two disadvantages:- you will have missed on the end-of-year planning opportunities- some of the most highly sought after professionals will be full and not taking clients anymoreAnd the longer you wait, the fewer choices you will have. 

I maintain even break even on valuation (which is rare in SF Zoned areas), the ADU has big disadvantages versus new property acquisition including financing, level of effort, rent control, prop tax being based on cost rather than value added, length of time including length of time from first expenditures to first income, reduction of something from existing unit (in your case existing home lost its garage).Did you see starting next year Mf can add an ADU per unit up to 8 units without any affordable housing concessions?

One of the disadvantages is if I add an ADU to my single family rental, it's considered a 2 unit and under rent control so I decided not to do that considering all the construction costs. 

A disadvantage to this type of investment is that it's likely your MOIC (Multiple of Invested Capital) will be lower than that of a common equity investment. 

Security deposit laws in Chicago are disadvantageous to landlords anyways.

you have an easy house hack opportunity that does not have the disadvantages of an ADU.  

Self employed and not self employed both have advantages and major disadvantages..

I definitely have some rose tinted glasses on and am drawn to the idea of 'lifestyle investing' hence why I am trying to get more realistic/experienced advice here.Kathryn and Jonathan, if I had to summarize your feedback;-If it seems so great, it will be competitive -If it is competitive, I am massively disadvantaged not being local/experienced in the market.