Or I try to find something that is in decent shape but because it is in a location straddling two different types of tenant profiles I can get a deal because it has the lower of the two tenant classes and ...

It's also a compounding problem.As deals become thinner, the ability for an investor to work with a competent and legal contractor becomes less and less... and so the contractors who used to 'straddle the fence' (so to speak) see their margins becoming thinner and thinner as investors push harder and harder.End result?

Depending on the answers above, your might want the easement to belong to the property and enure in perpetuity (if the neighbour is granting the easement to you or the driveway equally straddles both properties).  

If you want to live in the Andover area for personal (commute) reasons, then take steps to do so, and don't stay straddled between Andover and Central MA. 

If you rent the property out for at least 24 months (which is probably the most conservative timeframe because it straddles three tax years) you should be in a good position.

Not sure I understand the "problem" here.It's a deal like any other except that the transaction costs will differ because there are two different sets of local transfer and recordation tax rates.When a parcel straddles 2 jurisdictions the deed, etc. are recorded in both.You need to get past the 2 states issue and focus on the numbers.

The discrepancy comes either from a crappy experience, or realization that yes, purchasing cheaply is STILL better than just cash flow positive on retail priced asset.I've often wondered if I'm just straddling and noncommittal when I run TK numbers.

Always straddling the line of risk vs reward.  

Trying to straddle the line probably won't end up well.  

I would personally make sure that you hold for rental purposes for at least 24 months, which would straddle three income tax years.