Tenants intimidated by winos

I let and manage a number of apartments as a part of my job. A few of these are on the ground floor, just off a street that would be seen as "a bit rough" (although it is very close to city centre and I've always felt safe there). Winos have taken to hanging around outside the apartments and I don't know what to do about it. Last night (at 6pm) I was showing a prospective tenant an apartment and had to ask a wino to step aside to get to the door. The wino said something rude and then vomited on the ground right in front of the door! The poor would-be tenant fled without ever seeing inside the apartment. Other tenants have said that it bothers them and a few recently moved out because they said they felt intimidated coming in and out of the building. It infuriates me that we just have to put up with this. The guards have been informed but even if they did move them on they just come back. It is sheltered from rain, off the main street and is close to an off licence -an environment upon which certain sorts of unsavoury characters thrive! There are CCTV cameras but these people don't care. I know that there is no easy answer (or indeed any answer!) to this problem and that is why this is in Letting off Steam as opposed to Misc. Questions. When I was leaving, one of the winos followed me out and started begging for money and I saw two people stop and give him money - this really annoys me as they are supporting his lifestyle.

Can't you get togther with other landlords/owners and work with the buildings management to improve the entrance way, maybe adding a secure door?

I've seen some apartment complexes similar to how you described in the neighbourhood of Aungier Street and Christchurch. If theres a soup kitchen or a homeless persons drop in shelter which is acting like a magnet for these people your chances are greatly reduced of getting them to move on. I d say try to change the geometry of the entrance, making it harder to shelter from the rain and to sit down anywhere. You could install a slope on top of where a flat surface they might lie on exists, and use anti vandal paint, rough surfaces to make it difficult for them to lean against vertical surfaces. And move your gates out eliminating the porch. In certain complexes I ve observed this would probably work. I dont know about yours. Then get together with local business people and residents to change the tolerance for these behaviours , to report it more to the guards and report the winos for littering etc
Maybe also ask at local charitys which support them what pressure they can also apply. I also think the guards saying 'theyll only move back' is a cop out. The guards have a responsibility to ensure that once identified, someone who repeatedly breaks the law (intruding,littering and harassing inside your doorways) is made to respect it. And they have powers for this purpose.