In addition, your holding costs are way too low.Holding costs - Prorated property taxes, Insurance, Utilities, Interest on loans, LandscapingBest of luck!!

I think the relationship with the landlord was fine and dandy and then this came as a surprise addition (the "no friends/guests without extra pay" part...forget boyfriend...this holds true for her sister, mom, dad, ME!

Additionally, if you are able to become really good at navigating the new tenant laws this could be a competitive advantage for you.

Now, I know the object is to keep expenses low and profit high, but could a few simple additions increase your bookings?

Should I take out a HELOC or HEL on my primary residence, and use the funds from that to make a down payment on additional properties and then obtain a conventional mortgage on them?

Just completed a large remodel on my primary residence ($90k in) with the goal of refinancing to consolidate some personal debt and pull some additional cash for other real estate related projects, BUT ran into a road block with a lender.

(once I move out of the property and optimize the rental income from the additional unit)

The term "material amendment" as used herein shall be defined to mean additions or amendments to provisions of these Bylaws which-establish, provide for govern, or regulate any of the following:  (a) voting; (b) assessments, assessment liens, or subordination of such liens; (c) reserves for maintenance, repair and replacement of Common Elements; (d) insurance or fidelity bonds; (e) rights to use of the Common Elements; (f) responsibility for maintenance repair of the several portions of the Property; (g) expansion or contraction of the Property, or the addition, annexation or withdrawal of property to or from the Property; (h) boundaries of any Unit; (i) the interests in the Common Elements:

As long as the rent still covers the payments you should be able to leverage the money to either buy an additional rental unit (using that units future rent to help qualify) OR use it as a down payment for either an equity partner or hard money lender for a fix and flip in your area. 

One additional factor that helped me in the early stages of REI was having the advice of a trusted real estate agent.