I also have a variety of kilts and tend to follow the "right tool for the job" approach. I have a tank made to measure from the lady at "House o Tarten" here in Victoria - beautifully made and very expensive - I have several bespoke kilts out of Scotland in 16 and 13 oz as well. These three are my formal/semi formal wear ie for going to the club etc. I have two SWK kilts which I use for daily wear that can also be used for semiformal events. (These are heavy weight solid colour kilts, well built, fit nicely and dress up well - I love them and plan to buy another so I have a saffron, a green AND a black shadow tartan). I have a simple Black watch from Fantasia clothes - ebay special that is in a 12 oz - fits very well and is very comfortable but not great construction - good for around the house). I have three Freedom Kilts which are great for going out and about town, casual work situations and casual dinners - kind of like dress pants. (I think these are great- they are good for most occassions, really well sown, solid as a brick - they fit well and the service from Freedom Kilts is great. The shop is just down the street). I also have three utilikilts - a work kilt and two hiking kilts which are great for exactly that, home renos, yard work, hiking etc.
I have two Bear kilts on order - I plan to use them in similar situations to my SWK kilts. I also have a bespoke kilt on order in an Ancient Ulster tartan from Burnett's & Struth - I plan to use it for more formal occassions.
I guess this is a very long winded way of saying, IMHO what you start with depends on what you see yourself mostly doing in a kilt; formal, casual, walking about town, going to work, hiking, home renos.