i suggest using caution building/filling next to other structures in the event the new fill causes settlement of those structures. it doesn't sound like you have a lot of fill going in, but there again, the geology or site conditions and existing structures' settlement tolerances may say otherwise.
as far as constructing it, i don't any reason why it would be too difficult to construct. it will just take some good 'ole fashioned coordination by the contractor to keep from running over himself. if you happen to hit something needing undercutting/replacement, it'll get tougher to manuever...had this happen on project of mine through a swampy area. twas about 1000' long, ~24' wide. available soil and muck disposal was on one side of the undercut and street access/crushed stone was on the other all bounded by property line on one side of the road and swamp on the other. trackhoe couldn't sit in excavation since he would've sunk so the excavation had to be undercut/replaced in about 15' lengths (approximate reach of trackhoe) at a time. the contractor was finally able to work on one lane at a time so that access either direction was open. some places did require being excavated multiple times just because they couldn't completely fix it from where they were at the first time...in other words, there was some overlap in the middle of the road for the undercutting. your situation doesn't sound quite this involved so i don't see any reason (looking through the computer) why it can't be done.