Westwood, maybe I missed it, but what are the average trees you are going to be cutting? and what would be the Largest, you are likely to cut? What elevation are you cutting at?
If you are exclusively cutting 12-14" Pines, then a Husky 440 with an 18" bar would be plenty, if you are going to be cutting 18-24" Oak and Maples with some 36" trees thrown into the mix, the game changes very quickly.
If you are going to be cutting mainly small stuff for now, and expect to cut larger in the future, then I would second the recommendation to get a 450 Rancher now, and add something like a 562XP or 372XP in the future as budget allows for an excellent 2 saw plan.
Elevation can have an effect on performance as well. When I bought my 266XP the vast majority of my cutting was below 1,000' elevation, my 266 could bury a 24" bar with a full comp chain in a large Douglas Fir, and keep ripping. Now most of our cutting is above 5,000' in elevation, occasionally over 6,000', that 266 will still pull that 24" full comp chain, but it is noticeably slower.
We also prefer the larger wood that many avoid, if it is available and accessible, we will cut the 20-28" or larger stuff that many others drive past, I was seriously considering the 395XP, but Dave "The Chainsaw Guy" on here was selling New 3120xp's for $1399.00, and I was interested in getting into CSM (Chain Saw Milling) so for that price, I stepped up to the 3120XP, so for now, I am on a 4 saw plan, and in the Future would also like to add a 550XP and still want a 395XP too.
Becareful, CAD (Chainsaw Addiction Disorder/Disease) can be very contagious, you COULD even contract it from a site like this
Also, as has been mentioned PPE is an EXTREMELY GOOD Idea, a Helmet with ear muffs and a face shield, and a pair of Chaps, and some good gloves are reasonably priced for the protection they offer.
Doug