Maybe after this convo I will be able to loosen up a little, enjoy the process a little more, and actually pull the trigger. 

Or wait 12 months and see if you can get a Dorchester triple for $850K - I see prices sliding already and expect they will be at point where the math works in 12 months plus FHA is likely loosening requirements (PMI). 

Gone is the day of their money and your great deal for any one starting out for beginning.. although its loosening up as we speak.. but generally speaking someone doing their first deal needs to have significant cash equity in the deal to get a HML.And the whole reason HML work. is there are far and few banks that will do rehab loans.. they will do them for their top teir clients.. by top teir I mean HI wage earners or years of experience with that bank great cash reserve etc etc.. at least the banks I work with in our market in PDX... if you can get a bank loan then your financial houses is in very good order.. your character is impeccable and your capacity to do the deals are not in question. 

I know STR regulations have loosened as of recently and there are available permits in our sector for STR's.

We all know what happened last time lenders loosened up.

Lending will loosen in a few years.

You need to loosen up and come out of your shell.

@Eric Black ,It's my understanding that some lenders have loosened up their underwriting standards since 2012.

Lenders tighten up and when the market appears better then loosen up again.I expect the residential and commercial markets to keep loosening up.

I have been hearing that lenders are loosening, and as foreclosure/short sale credit issues start coming off reports in the next couple of years, then buyers may start flooding the markets, pushing us buy/holders out.