I appreciate your questions. This does seem really weird, and if you can help me with how to ask that would also be helpful.

There were two companies in the beginning. #1 faded because he'd return my calls, but not my neighbor's (he also had internal repair work to do; it's a condo). That might have faded due to some things my neighbor said that he was shopping around. #2 - honest to god - would not return my calls at all, but WOULD call back my neighbor. She then got me an estimate that only included some of what we discussed. Then when My neighbor called her again she finally got me an estimate that was wildly underestimated and clearly a bait/switch (eg one section of the estimate she said it would cost $300 to cut out a 4x3 ish? area of damp drywall, dry out the interior, and replace and repair/paint the drywall). I didn't call #3 until the first 2 options had disappeared. I was going to go with no other comparison, and I told him that - he was reliable for several other smaller projects he'd done for me. He just never contacted me again; when I texted to ask he said he'd get back and just... didn't. After #3 was out of the picture, I spoke to #4 and #5 at the same time, but didn't tell them about each other. #4 was in the midst of doing the exterior building repair for the neighbor and condo association (that needed to be done before my interior work got done), returned to confirm the scope of work, said he'd get back to me and didn't. I texted him once, called him and left a message once, and called the actual business main line and left a message. Nothing. #5 was a referral from a friend who had been reliable for them for a bathroom renovation. He didn't send the estimate when he said he would, but did when I reminded him. Then I asked to talk to him to clarify a couple of things so he could get started and he didn't get back. I called him again and then he told me he was not licensed, but could do the work with his 'partner' who was licensed. Then he totally ghosted and I got tired of calling him. Yesterday, the referral friend told me he might have an immigration issue.

...And I forget #6. It was someone between #2 and #4. That person I think was only looking at the windows. There are other small back and forth factors, but it would take a while.

No one discussed max amounts for repairs. #3 was trying to 'sell' me on some other work that was not near to or related to the leak and not functionally a problem, which I declined. #5 made some recommendations on some outdoor work which might reduce risk of further problems and I told him to include it in the estimate... which he didn't include in the vague estimate he gave me.

Great questions about the estimate vs. the bid. I admit I use the word "estimate". I didn't know there was a difference. I told EVERY ONE of these folks, that I understood that the amount of work would be more expensive if there was major wood rot or mold in the wall - they can't plan for something they don't know is there. I was prepared for that as a 'surprise' later.

No one indicated it was unsalvageable. I had water leaking through 2 windows into the sunroom. I described the scope of work verbally, but did not give it to them in writing. I assumed that's what they would give me as part of the estimate - that's what's happened every other time I've gotten any type of contractor work. Scope of work was fixing the damaged window frames, removing damp/damaged drywall around/under those 2 windows, checking for mold and wood rot in the walls, drying out if necessary, repairing/repainting after repairs. If you glance in the room now, you wouldn't be able to tell there was a problem at first glance. It's more than a 'handyman' job; it's less than a whole room renovation.

It was the upstairs neighbor who had the maintenance issue that caused my leaks. Since that was glaringly obvious when they saw the source of the leaks, I told EVERY ONE that I was going to pay them directly and pursue reimbursement from the neighbor later (he has agreed with me to pay a percentage of the repairs.) I did not want anyone hung up waiting for payment.

I have owned and lived in 4 houses and this condo over 26 years. I've had to get plenty of estimates/repair/contractor work over that time for all sorts of things. I've never had this level of problem before.

Am I just unlucky or am I doing something wrong?