SVN driving me nuts, cleanup? Obstructed? BS! (Windows => Unix SVN)

Greetings,
     I've spent the last 3 or so hours trying to get something trivial
done... I've worked with the following Version control systems since
1984: RCS(unix), PVCS (DOS), RCS(DOS), PVCS (Windows), Source-Safe
(Win), and Perforce (Win), CVS (just to do a sup), and now Subversion.

   I'm using the latest TortoiseSVN, as of 10 Pm Sunday. (Info at end
of e-mail)

   I had someone else setup the port on FreeBSD because, MUCH to my
amazement, it is the first port that I couldn't just do a 'make
install' and have it work out of the box, without any issues.. In
fact, it blew up and had to be manually configured (default was for
Berkely database or something, and required some plug-in into Apache
that wasn't the default, and wasn't obvious how to install. - I've
installed maybe 50 other ports - one of the things I've loved about
FreeBSD since the first release that I install - 13-15 years ago..

   So, what horrible complex thing am I trying to do that keeps
blowing up TortoiseSVN? Well, my brother created a repo. and checked
in 5 projects into it.. However, he checked in the 'bin' and the 'obj'
directory as well... I wanted to remove them... So, stupid me, I
clicked on the directory and did a svn remove... and tried to comit
those changes... Somehow, I got a obstructed directory... Not sure
what exactly that is, but it wouldn't let me do anything with it.. I
tried to clean it like it said, and the clean failed... (I hate to
ask, why can't it clean up after itself? If the check-in fails, it
seems like it should just roll the checkin back, and everything is now
OK, EXACTLY like it was before the attempt, let the user handle it.)

   I finally fixed the obstruction, but doing 'rm -rf work' and
starting over, then just going in and removing the directories and
comitting the change after each removal. (I'm not exactly sure why,
but the 3rd attempt at removing the directory actually blew away the
directory locally, but the first two didn't...) I might have blown
them away using the repo browser... Maybe that caused the obstruction?

Ok, now I have a fresh directory, I did a compile in it, and tried to
check in the changes... It said there were a bunch of non-versioned
files (all those in bin/obj directories) I did an ignore on those...
also ignored a single file in one directory... And tried to commit...
the directory that had the one ignored file now was showing as
obstructed... Doing a clean failed as usual...

Back to doing an 'rm -rf work' for the 3rd time.... And I'm to the
point of ranking Subversion as "Pew!", right there below Source Safe
as the new worst system I've ever used....

But I'm really trying to figure out if it is just TortoiseSVN that
sucks, or is it subversion? Up to this point, I was really impressed
with TortoiseSVN...

So, my questions would be:
     A. I've heard good things about SubVersion from multiple people,
am I just having HUGE amounts of bad luck? Or does it really suck?

    B. TortoiseSVN / SVN seems to be as fragile as eggs, maybe more so
as so far I've not gone 30 minutes without some sort of a obstruction
that is causing the whole directory to need to be blown away. What
is making it so? Surely, it can't be that bad and still be so
popular...

    C. I switched to cygwin's ssh because the one that shipped with it
was worthless - I got prompted 15 times in a row for a password when
opening up something, at least with cygwin's version I was able to
just see 15 command windows popup.. Sometimes multiple ones active at
one time.. This didn't impress me with the quality of the software to
begin with... I was in a situation where I didn't mind keeping the
password on my machine.. (or prompt for it and keep it only for the
next 10 minutes or something..)

    -Chert

---
www.traderhut.com
PS: Here is the info from the about box.
TortoiseSVN 1.5.3, Build 13783 - 32 Bit , 2008/08/30 20:59:46
Subversion 1.5.2,
apr 1.2.12
apr-utils 1.2.12
berkeley db 4.4.20
neon 0.28.3
OpenSSL 0.9.8g 19 Oct 2007
zlib 1.2.3
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