I know you said you're looking for training but another important thing to ask yourself is what other kind of support will you want there are so many things to factor in if you are planning to do real estate as a career. 

It doesn't seem too me that there is a infer-able motivation factor here, but I think they are great data points to refine your marketing strategy by.

This stuff is DURABLE, easy to lay down, warm and looks just beautiful.  

An S corp would offer some protection, but if it's actually worth it is very situation-specific and depends on other factors including how much income you receive from your W-2 job, etc.

I've seen a video on youtube froom "Commercial Property Advisors" saying that it is actually better to buy a 5+ until as opposed to a 4 unit building because then the loan is commercial and the property cash flows factor into the evaluation of the property in underwriting (in addition to you still being checked out for income, assets, debt, etc.), whereas with residential, you can qualify for residential on just your income and assets alone, no evaluation of the property.  

Beautiful home, excellent bones, built in1920, super well maintained, original woodwork, a few stain glassed windows adding character, etc.  

We currently do factor in 10% in our budgets for surprises.

The beauty of this second purchase is that is is located in a better neighborhood where the residents are longterm tenants/homeowners.

I told the new buyers that this was one factor that said that this was a good property to own. 

I think it would be an ok block for a buy and hold, but that block does not have the ...not sure how to say it...the beauty of some of the other blocks, thus will not draw the higher prices some of the other blocks will draw.One thing though to be aware of is where the historical district boundaries are.