Thank youI know the rents and specifics of the units Im more interested in bringing in a partner or private money to get started but will definitely compare it to financing.Again, thank you for the great insight!

Two questions:Would this purchase be considered a "second home" (for tax/mortgage purposes) even though I don't own my primary residence? 

It skews it a little bit when you are comparing apples to oranges due to future expected maintenance costs. 

Ideally ones that specialize in multi families of 20+ units.Hoping to find a few and compare quotes.

I think it is much easier to understand not only the markets but the laws of the state you live in compared to crossing state lines.

Use of Lots.The Lots shall be occupied and used as follows:(a) No Lot (as "Lot" is defined in paragraph 1 (b) above) shall be used except for single family residential purposes.

Which career path do you think is reasonable for my purposes?

(If new tenants don’t take over, then 1 month rent can be withheld for marketing purposes, etc)Then gf/sister sign new lease starting on the same date.

It has no relationship to the actual market value of a property.To figure out your true market value you need to look at the most similar and nearest comparable sales.

What IS the purpose of the assignment clause?