No, you do not need to use the word 'condos' in each breadcrumb but it is necessary once in the highest sub-folder possible to prevent duplicate URLs.
Having it as your H1 will indeed be enough for search engines to recognise that for what the page is about, however you will get an extra ranking boost for it appearing in the URL also.
If you leave 'condos' or 'homes' out of your URL all together then you will end up with duplicate URLs as they will both be something like this for both homes and condos:
http://www.honoluluhi5.com/oahu/honolulu/hawaii-kai/hahaione/
This will break the functionality of your site and you won't rank, of course. The reason I use this example:
http://www.honoluluhi5.com/oahu-condos/honolulu/hawaii-kai/hahaione/
is because it incorporates 'condos' into the URL whilst keeping the URL as short as possible and using your keyword as close to the top level, which is the most optimized way of doing it for your keywords (Condos in 'location').
Nice, tidy, short and clear URLs that explain what the page is, whilst hitting your keywords are the goal
I currently have two real estate clients with this format for example: www.domain.com/new-homes/location/property/. This usually results in higher ranking for 'new homes in 'location''
If you don't think it works for you that is fine, it isn't a huge deal providing you are succeeding with other ranking factors, but it has had proven success for me in the past.