Winterization (summer cottage) pro vs DIY approaches

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Hi again, still love this community AND the well-organized platform + moderator.
Pardon long/complete? description, I always include TMI, it's a curse and a blessing.

My sweetie/GF has a summer/near-beach cottage in York, Maine, USA, built early 1900's initially w no plumbing! Minimal plumbing now >50yrs-old pipes, with ( kitchen sink ; elec water heater ; bathroom sink + toilet ; shower ; garden hose spigot) all reachable under the house/floor (house is ~3ft above ground). Unusual? town seasonal water pressure/SUPPLY feeds this+other near-beach neighborhoods. In October: the town shuts the per-house valve on street and takes the water meter away (near house at ground level). April: town reinstalls meter, leaving shutoff valve closed (shown in pic, hand-turn valve).

WINTERIZATION/October by pro's or DIY steps for us: close shutoff valve in advance of town work if desired, or wait for meter+pressure to be turned off by town. First, turn off WH elec breaker and drain WaterHeater. Attach air compressor to 3/4" female threads (house incoming feed) where the water meter usually attaches (circled in pic). Drain/empty toilet tank, pour some RV fluid into toilet bowl and each sink + shower drain. Run around blowing air out of each fixture (one at a time being opened, so all the air pressure is used to blow-dry each fixture one at a time). Finish the air-compressor HOUSE-blow-dry by opening the final drain valve under the house. FINAL step AFTER town turns off supply: because town-water-feed = black stiff-rubber?plastic? hose, switch to air compressor blowgun nozzle w rubber tip. Shove a long (our feed is 25ft long) skinny hose down/inside the 1/2" ID feed hose (which also contains shutoff valve which is less than 1/2" ID, and complete final street-feed-blowout step.

SPRING/April "TURN-IT-ON" is so simple and tool-free: wait for town pressure+meter with shutoff valve closed. Check that all fixtures + final-house-water-drain-valve is closed. Open incoming valve to let water into house ; crawl under house listening for possible air noise ; if none, open garden hose spigot until water comes out then shut off spigot. Reinspect under house for unlikely broken-pipe leak. Open kitchen faucet hot + cold valves until cold water comes out, then shut cold valve. Leave kitchen faucet valve open until WaterHeater fills and sends water into kitchen sink. (Now turn on elec HW breaker). Continue to use cold water and purge air from all fixtures. (avoid later hammering; haven't seen/heard any yet).

OVERALL QUESTION: who has experience (owners hiring pro, or pro doing/charging customers) doing or getting this service? Our pro plumber charges ~$350 for 2 guys to spend under 1 hour in October, plus they coordinate with town for timing. I've watched/assisted this for the past few years/Octobers. OK/whatever$, but Spring opening does not require pro help, in my opinion (I've turned things on myself the past few April's). HOWEVER, our pro plumber went hardball on us and said they REQUIRE us to have them do spring/April turn-ON "due to insurance requirements" (really? am I getting a guarantee than any winter-cracked-pipe,etc is on them? I don't know yet, but I am starting the process of ditching pro service completely. Anyways, another $190 they want for too-easy quick April turn-ON. SO...(Q) to rephrase, what do you think of this must-hire-and-pay-each-Spring-as-well policy? Plus, any other feedback I'd love to hear. I'm still prepping to go DIY next October, haven't bought a small compressor yet, don't want to lug my 20gal compressor to cottage since I can afford a use-1x-per-year small compressor. (if it matters what brand to buy, I'm listening.) I'll use a 3/4" fitting, believe our house has GHT female (circled in pic), will doublecheck this weekend w MGHT fitting. Google says "Garden Hose Thread (GHT) comes male (MGHT) and female (FGHT). It's important to note that GHT is different from NPT. Garden hose connections are not compatible with NPT even though both are threaded."(google result). I know that NPT is tapered thus is the irrelevant type for me/here.

TMI#1: I asked the pro during October winterization: what size hose is that, (fits inside the street-fed hose 1/2" ID), he said 3/8" (meaning, ID i think). But his hose must have been less than 1/2" OD. I'm forced to use a hose/tube less than 1/2" OD, and a skinny-walled tube seems best since commonly-found strong/thick-walled 3/8" ID, 1/2" OD tube (like in pic) goes in initially but won't go thru the shutoff valve. I just rcvd a Metaland(China) 5/16" ID / 7/16" OD Silicone Tubing (hose) ( 32.8ft for $25 amzn, hardware stores want $1.50/foot for similar stiffer hoses, thin = polyethylene) which looks promising, delivers a good air flow at 60psi with my big compressor via rubber nozzle tip. Hope it fits in feed tube all the way to street. If I had to use 1/4" ID hose, I suspect the blowout process might not work OK due to such a restricted/small size opening, but that's probably me being paranoid.

TMI#2 from here down, mistakes = fun story?
I got involved+around (me: DIY idiot/brave) a few years I goofed once, then we keep/kept calling the pro/plumber(s) for winterization, we can afford it but still feel it's throwing $ away. My confession/idiot-story, which justifies my GF's tendency to keep paying pro, though this is the first year they've insisted we pay them in April too if we want their future service: One time (Oct 2020) I got brave/dumb thinking I could drain/vacate the pipes myself (I once had a lake house which I could gravity-drain with no air pressure required..cheap ancient 1/2" PVC survived every winter). For this cottage, I never even thought about the feed line, both mistakes very stupid BUT and SO... Over that winter, the feed line (unpurged, thus full of water from street to near-meter shutoff valve) somehow did not break. (regardless: lucky-once, I feel this is an important step). What DID break that winter, my fault, was bad: some cast iron pipe areas under the house were NOT purged by my no-compressed-air attempts to drain, so they cracked and broke. So we paid the plumber $1200 for a handful of repairs under the house (so now there's a mix of iron,copper pipes spliced to new-PEX sections). I love this cottage. (she lives in MA, I live north in ME! We don't rent it out.)
 

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