With my interest in learning more I have researched or looked for jobs nearby but I have noticed that the design community in Eugene is fairly small and most seem to only be a one person job.

They allow up to two dwelling units per lot but that seems to be more for like a finished basement unit.

It seems like it basically up to you to do the math on how much more you will potentially make selling each unit individually and then deciding if that extra $$$ is worth the number of extra hours you will spend.

So many people gloss over properties before truly evaluating their pro forma rent.Also, I think it's a great point about this strategy working in higher rent/gentrification areas of Chicago..it seems counterintuitive.

It seems too good to be truth for me.....  

Your goal of buy and hold and flipping so soon seems very difficult, especially with a young child (our first is due in January).  

Aha it seems like every time I sell one of mine its the time.

It seems the only people who actually got loans from them were PPP loans from the government during Covid.

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It may just seem like a small amount because the properties there are pretty cheap, but if you back-calculate the property tax rate, it's relatively high (not Texas high, though).