High leverage in cyclical markets in peak cycles can be problematic.You situation appears to revolve more around adequate liquidity.  

Taking on a project like this that MIGHT eventually give you a positive cash flow in the sweet bye and bye (but continuously drains my wallet for goodness knows how long in the meantime) does not sound like any sort of a deal to me.

When/if your home appreciates refi and make the PMI go bye-bye.

I did at the peak of my career have over 300 units I personally owned and managed.

There's nothing like someone showing you a potential deal to peak an investor's interest.

Also check out my favorite "Best Market" lists for a quick peak into how I started looking at this (Texas is the clear winner here but I find it difficult to do business there right now).

I realize I'll be looking for tenants outside of peak rental time.  

@Robert Sims...Lesson learned..Most will offer something to peak interest, but due diligence necessary.  

There are also people who just break even but they use it for personal use for a chunk of the peak rental season.

I heard Ann Arbor is an up-and-coming market with potential for ongoing future growth, whereas, Boston may already be saturated and reached its peak...?