I've only taken up astronomy in the past year, and have learnt a lot from reading and experimenting. My interest was kindled by an impulse buy of a kids' NG scope on the high street. Total rubbish, but it got me hooked. Couldn't stop waiting for a clear night to look at the moon. Wasn't sure what to get next, but found a retailer in Bristol with a Celestron 76AZ for just over a £100 which seemed a good next step. The tripod isn't that steady, and the AZ action is far from smooth. However, I saw Jupiter and its main moons for the first time, and some decent moon views. A charity shop buy of a scruffy 1980s TOWA 60mm refractor led to much dismantling, cleaning and replacement of missing components. This scope is always going to be special as I saw Saturn though it for the first time. Attempting to improve the Celestron I managed to damage the secondary mirror mount - fixed with a washer and Araldite. At this level, learning costs are manageable!
Determining that planetary observations are my main interest helped to narrow down the next purchase. But I still took months agonising over it! Perhaps that's my main regret. I did get a great FLO offer on 6 inch dobsonian last month, but have had limited opportunity to use it due to cloud. Initial use proved this size to be the limit for me to carry and use comfortably, so no regrets there thankfully. Great views of Jupiter too.
The one thing that has struck me in Astronomy magazines is the lack of objective reviews. Camera magazines are full of lengthy reviews with regular summary tables of features, ratings etc. The best we get are usually short setup commentaries, which are not really what we need. I can't get out to night time events, so traditional astro clubs are not a viable try/see approach. The only retail showroom with kit to try was Jessops (don't laugh!), but they've closed in Bath. Some websites are shallow re-hashes of manufacturer info; others opinionated and look down on lower end equipment. Reviews of cheap telescopes on many general retailer websites get 5*, and they either misguided, or have very low expectations. But there are some good sites, SGL included, which helped with the pre-purchase homework, and avoid buyer's regret.
Let's buy what we can reasonably afford and enjoy the kit every evening the skies are clear. Hopefully that avoids any serious regrets ... and keep us happily gazing into the skies ... and that's what our hobby is about.