Keep in mind that Hunting Point Towers were built in the 50s, so of course they have issues! That should be immediately obvious to any prospective renter. Its probably one reason the rents are so reasonable. This is not the Taj Mahal and you are not going to be living like royalty. Its a old structure with a fresh coat of paint. I took that all into account before signing the lease. Apparently others on here have not.
As far as bugs, I've lived here since the summer of 2011 and only initially had a roach problem. If you keep your place clean and your kitchen immaculate you will, like me, rarely if ever see a roach. If you are used to leaving food out or putting organic food waste in your trash bin and leaving it around...well you're going to have a lot of insect company.
Maintenance has never been an issue for me. On the contrary the public areas are far FAR cleaner than I've seen in many higher rent communities. Its obvious the staff takes pride in their work here. Do the landlords enter your apartment when you are away? Yes, when they need to--as landlords have a right to do. There have been several times I've arrived home and could tell by the way the doors were re-locked that they were in (after the earthquake and when the place above me had water issues are the two recent examples). Nothing was stolen and they cleaned up behind themselves when doing work.
Residents here are friendly and you can't beat the rent. True, the kitchens are '50s vintage so no dishwashers or food disposal units. But the appliances are new and the parquet wood floors throughout the apartments are beautiful. The large windows in the living room let in lots of light and the A/C units are new. The biggest selling point for me is that these towers are adjacent to Old Town and right on the Mt Vernon Trail. As an avid biker and runner, its nirvana.
If you don't mind not having to pay for dubious amenities like granite countertops or other fancy things, but do like the outdoors, then this is the place to be.