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I view it as a NNN investment. 

Also, your taxes will be stepped up after closing, especially in an appreciating market (as you describe it). 

Many are also offering above my asking rent, paying up to 6 months rent in advance, or even submitting applications without viewing the property.

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But fundamentally I don't understand the strategy from a sustainability view.

Up until now my point of view was that it was a good summer to take some $ off the table thanks to the bidding wars driven by anxious people scared of “missing their chance”.

Its market and local code dependant for all other then the (in my view and most code) the GFI's in the bath, kitchen, exterior/garage/basement outlets.Buying an older house has more expenses vs post 1970 which is when most systems are all up to snuff;  plumbing is largely copper, decent circuit breaker boxes and amperage power feeds from the street, sewer largely PVC...   

@Jaime Rossini,  there is a lot of info missing in your post to allow a full assessment but here is how I would look at the situation if I was to buy with a view to house hacking (live in the vacant unit for a couple of years).Regarding the purchase, this is how I would determine how much gap financing I would need.Purchase Price + Closing Costs for purchase and new mortgage + Cost to Upgrade vacant unit - How much can I afford to invest as my own initial equity?

I'm sure there are books that are written about seller financing, but I haven't come across one yet that describes the way I do it.I would recommend Algebra and Geometry.