My point in saying that, is a lender may not be comfortable stretched to 80% of acquisition without any interior knowledge and this market in particular.Your best bet is a local lender who won't require an appraisal.

I have thought about buying a multi and house hacking but I live in a very pricey market (NYC) and would prefer to stretch out my money in a less expensive market while maximizing my ROI/cash flow.

But it would allow me to stretch out my student loan payments, increasing my cash flow now, allowing me to save more money for more properties. 

Each lender has their own idiosyncrasies in this are: some only accept signed fixed term or annual leases (i.e not month-to-month, even if it is written); some will accept estoppels from month-to-month and long-term tenants w/o a written lease; yet others will require estoppels in addition to the signed lease {to be certain there are no verbal considerations being given to the tenants that are not reflected in the lease}.In the couple of instances where we were stretching ourselves (acquiring two properties in the same month, closing the same week), we made signed leases and estoppels a condition {just tell the vendor, your lender is insisting} and offered to collect the estoppels ourselves {which you want to do anyway}.

As for getting a loan, that's generally advisable as it will let you stretch your investment dollars further.   

Stretch to make this happen, ensure you have adequate liquidity to survive any bumps you may encounter down the line and you should be happily pleased in the end.   

I asked if this was something that the title insurance policy would take care of and I was told that "this is not a title issue or claim by any stretch"    I'm either ready to call the title company myself monday morning or get a new attorney. 

When you aren't living off the cashflow, then even if you have a rough year, you had good years before and after that year to make up for the bad stretch. 7.

And thats stretching it.

And I know it is a stretch coming onto a forum (trust me, we are looking everywhere and trying everything) but we are looking for any potential equity partners in the Long Island area that would want to go in with us on a few projects that we already have lined up.