I need a reality check on something unpleasant that happened today
with a roofing contractor. Did I err or is he being a little hinky?

I've been renovating my 100+ year old Victorian (new siding, new
windows, etc.) There is a small mansard roof at the front of the
house, and the historic slate and underlying tin were a mess. I
located a slate specialist and also got my neighbor (whose house
adjoins mine) to agree to do his mansard at the same time. We got a
small break on the price from the roofer because it originally
appeared both could be done at once. The work was going to be
approximately $2,200 for each roof.

For about a month there was a hassle getting my GC and roofer to agree
on who was doing what first, but in the end the GC had to rebuild the
roof deck and reinforce the rotted vertical structural supports before
the copper gutter, downspout and slate could be applied. Because the
tear-out was so extensive and we didn't want to leave the roof open,
both roofs couldn't be done simultaneously as we had planned. I
offered to pay the roofer the difference but he waved it off and said
he wouldn't charge if it it didn't make a difference to his final
profitability on the work, etc.

After a few delays on his side(some weather-related and some not) the
roofer finally came out last Friday and Saturday and installed the
slate. The project is not quite done -- he needs some additional
contrasting slates for the decorative rosettes and has a small area
adjacent to my neighbor's roof which needs shingles -- but he included
a small holdback in the invoice for the last bit of work. Everything
looked great and as he was packing up on Saturday, I offered to write
him a check on the spot, which he declined because he wanted to double
check the invoice before he sent it. I also asked if he would like to
stop by next week to pick up the check. He declined that also.

The roofer FAXed the invoice a day or two later (Sunday or Monday) but
I was so swamped at work over the next few days that I didn't have
time to sit down and write out the check until this morning
(Saturday). The roofer had called once on my cell and sent one or two
E-mails but I couldn't even listen or read the messages through until
today. Even then, they weren't along the lines of "Hey, I haven't
received payment yet. When do you think you can send a check."

I sent the roofer an E-mail this morning letting him know that I'd
torn the house up but couldn't find the FAXed invoice and asked him to
please reFAX it or E-mail it. I got back an E-mail stating "please
send this out immediately. I operate based on volume and the process
I created requires all aspects to function fluidly...unfortunately
this has not happened this on this project. I don't feel that it is
any one person's fault. Regardless, my profit (and scheduling) was
based on the two projects together. We have already discussed this so
no need to reiterate. But, in my business money is constantly
moving, i.e. payroll, materials, and you need the flow to remain
constant." I immediately called him and asked him what on earth was
he upset about, and that's when he went off about the contract stating
he was supposed to be paid upon completion and that he'd been stiffed
before by some woman for a $27,000 roof, and that he had to make sure
he did things promptly so he could file a mechanic's lien, etc. I
told him I was sympathetic about cash flow as I used to be a
freelancer but was offended that he assumed I was going to stiff him.
Among other things, why would I have E-mailed him asking for another
copy of the invoice? And why would I have offered to write him a
check on the spot when he finished the work? And finally, he's still
holding a deposit for my neighbor. Like I'm going to cheat him even as
I'm working with the GC to get the prep done on my neighbor's house.
I told him to come on over and pick up the check if things were that
desperate but once again he declined. He was too busy.

This afternoon I took the $1,200 check to the post office and mailed
it, which is exactly what I was planning on doing anyway. But I'm
still upset. I've never cheated anybody in my life! Was I committing
a cardinal sin by putting the payment off a few days (5 days at most)
until I could get to it, or is something else going on here?

I do want this guy to finish the work because of the quality of work
he does, but how do I approach him to (1) come back to finish my
section; and (2) get him to start and finish my neighbor's roof. He
already told my GC that if the guys can get the neighbor's roof deck
rebuilt before March 27 he could come out on a Saturday and get the
work done. My neighbor does have a signed contract with him, so
should I let him communicate directly with the roofer? I hate to put
the onus on him as he is so far away.

Any insights and strategies would be appreciated! And if I was wrong
let me know. Thanks!