Commentary On Watchmakers, Service and Price

Over the last three years I have established a relationship with a watchmaker whose work I trust. Lately he has been taking way more time to complete jobs, and has not been returning calls. He has had my UG Trii-Compax since October last year. The shop is still there, but it was locked during his Saturday open hours. I was able to get in touch with him last week (when I blocked my number-is he ignoring my calls?) and he said he hoped to have a watch completed for me that weekend.
A friend passed along info about a watchmaker that was recommended to him. I checked out the ratings for the new watchmaker and the majority of the reviews were excellent. He is a Swatch-trained and certified watchmaker with a diploma from AWCI in CW21...well qualified to service mechanical watches.
For reference, I took a Longines steel wristwatch with an automatic caliber 341 movement to the new guy for a quote. My watchmaker would charge me about $80 for a movement service and take two months or more to finish it.
The wife (and battery/strap changer at the shop) took the watch to her husband. Through the glass I could see him look at the case, give it a shake, listen to it briefly, and hand it back. The watch is a crystal-lift front loader (not quick to see the movement) but I told the lady it was running fine if not a bit slow, and the service history was unknown.
The estimate was $275 and a five week turn around.
I expected a high quote for the average Joe (sorry, Joe), but I thought that seemed waay high.
As I chatted with the lady, she mentioned her husband had some watches for sale he would need to service. Finally I got to chat with the watchmaker.
He was a very pleasant but clearly busy technician. I was completely transparent with him, mentioning my collecting experience and my familiarity with watchmaking and its language. He seemed at ease discussing his business, even alluding to more favorable pricing with establishing a relationship.
He even had a watch I liked, and offered it for $375 after he completely serviced it. Trouble is when I get bored and go to sell it, it might achieve $250.
So I'm thinking...do I buy his $375 watch, and look at it as a $250 watch with a $125 service, to begin establishing a relationship? Or accept that a Swatch-and-CW21-certified technician commands $275 for an auto time-only movement clean/lube/adjust/warranty and just pay it hoping the price comes down with subsequent visits?
I am a chronic flipper, so service costs definitely come in to consideration. I only service the pieces that need it to function correctly. At $275 I think I'll live with my slow Longines until I get bored and sell it as-is.
Or stick with the guy who does good work cheap but takes way too long? Considering my flippertosis the pricing really makes a big difference, but sometimes the time it takes is just too much!
If you're still here and awake, please comment on any (or all) of the stuff I mentioned. Curious to know others' opinions!

Buy the $375 watch and establish a relationship.

There's a Russian father/son watchmaker team near me, and the father is notoriously rude. I bought an 1884 Waltham pocket watch with paper warranty inside that Dad had restored, and things warmed up considerably. On my last visit the son showed me ~20 Omegas he had picked up at the Las Vegas show (including 2 solid gold) and gave me first crack at them before they went up on eBay. Relationships are everything.

I think when buying a anything from someone then often it is the personality of that person that is important. A bit like as someoneon the forum has said you are buying the seller as much as you are buying the watch. (I can t remember who said it but it is excellent advice)

He's had your UG for 8 months?!?

A friend of the family's UG, actually.
I warned him from my experience that repair on a UG Tri-Compax could be lengthy.
The movement needed a part (I forget which), and it took my watchmaker six months to source it. Now we're running at two months for the repair, which is the norm for this guy.
So actually, it's business as usual, but all totaled 8 months feels like an eternity.
Coincidentally, it took the Henri Stern Watch Agency 8 months to service my Patek Philippe Jumbo Nautilus "Comet" 3710. I should be used to such experiences by now...

I could see buying this particular seller/watchmaker, but the price seems high. Maybe I get what I pay for? I suspect the quality of his work is exemplary.

Ahh, the missing part that needed sourcing explains the delay. I was going to say...

If you are getting watches serviced regularly and possibly sending business his way via friends then I suspect he will give you a good deal without you needing to buy from him before hand, especially if you don t really want the said watch or are intending to sell it on in the near future