Refusal of Entry clearance UK border and EEA unmarried visa

Hi all,

My boyfriend who is an American Citizen tried to enter last December with a standard tourist visa in UK. Unfortunately, he got refused because he said that if he likes here he would like to intend to find a job for a year or so. Of course, with a tourist visa you cannot work and we didn’t try him to work without a work visa. He just wanted to see if he really likes here to be able to leave and come back with a work visa.

The officer put the stamp in his passport but in the last question my boyfriend said that he didn't have a return ticket because we were leaving UK in 4 days to go to spain for Christmas. I thought as he was leaving the country was not necessary to have return ticket (I think this was the main mistake). At the end, he was returned to USA and he ended up getting another flight in the USA to come to Spain for Christmas and he didn’t have a problem there. we spend a total of 20 days there.

Then, an officer advised me to apply for EEA family permit family, I knew that we had a chance to be denied too as we were applying for unmarried partner and we have been just living a total of 1 year together in the US instead of 2 that it is what you need for getting this visa. We tried because we thought we didn’t lose anything. This was not successfully because we were not consider as “durable partner”. He got denied for this visa as well, on the 3/3/15.

Now, He has rented his house for 6 month to come as a tourist visa again this time I am working (I was not working the first time he entered because I just got here from America) and he has savings and we will have a little bit of income every month for his rental. We also want just to be here for 6 month as we are getting ready the papers for me to come back to America. As he got denied twice,I am really afraid that he won´t be able to enter this time around. (We also have intention to travel around Europe during this 6 months)
Could he have a problem at the UK border?
Would it be easier if he takes a return flight for 1 month instead of 6 and then go to immigration office to extend his visit?

Please any thoughts/ advise would be appreciated!!

Many thanks!