I'm not quite sure why he bought it to begin with, I haven't asked him that yet as I feel that's a bit intrusive (maybe I'm wrong?).

Look for telltale white spots, efflorescence on the lower part of the basement walls that commonly indicate the regular intrusion of water.

We have been getting the place ready for rehab and there was significant intrusion of vegetation etc and to preserve the integrity of the roof, siding and fascia trees and vines need to be trimmed/cut.

It needn't be intrusive but at least once a year.2.

However, I include a request to not walk the property prior to our showing appointment out of respect for the safety and privacy of my existing tenants also living at the property.Maybe a RE agent out there has another angle as to why they would be so intrusive about the ID up front without at least some inside pics and an amenities list.

This will ease any feelings of "intrusion" they may have and if not, that's their problem.

These are moderately complex - rewire, replumb, water intrusion, rotten kitchen and bath floors, reconfigure for master ensuite, and open kitchen/den.West End is very hard -- 100 year old homes, so lots of complex framing issues, super competitive, and require full gut rehabs or pop the top.  

Just a rough wag for now, but at least 10k for repairs/updates if no major intrusive work has to be done on the plumbing.

The inspector said the house needed a new roof 5 years ago when I bought the place…When I walk on the roof there are areas of clear rotting in the sheathing under the shingles, it’s spongy as if there has been moisture intrusion and rotting of the sheathing…The roof is bowing in some areas also, and has a couple of curled shingles.

I don't want to be intrusive but want to make sure our properties don't get run down or have a problem linger that maybe the tenant doesn't think is a big deal but I will want to address right away.