This is just my opinion...I would not....simply because from what I have seen, those fences peel quickly..I am not sure if it is the kind of wood they use or what. I have a white painted picket fence, and it has been about five years and it has not peeled at all. But I have driven by many of homes who have painted the kind you have and seen them peeling and looking awful...not sure why..maybe it is just poorly prepared surface..but I would not want to risk it. I also have such a fence on my property edge. How about concealing it instead..Use plantings to soften it and hide it..tall grasses..roses if you have good sun? Even just bushes as a backdrop. You have nice bones to your yard..I think you can make a lovely cottage garden fairly easy, just remember the single most important thing as far as I am concerned, is the soil...with bad soil your just throwing away your money...so add soil and ammendments BEFORE you spend much on plantings so the money spent there survives... I wouldn't paint..I would conceal...lets its natural beauty be a backdrop..it just looks bland because there is nothing green in front of it. You can also use trellis and or hanging things on the fence to distract a bit from it too. Old windows..rusty iron or pieces of tools..colorful birdhouses...lots of choices...good luck and share your progress and pictures..and never hesitate to ask...I have learned so much from these wonderully warm and knowledgable people. A bit of advice..dont try to turn your entire lawn aroudn right away....big job, large expense..instead choose areas..and do those areas over the top....then move to the next.....and be sure you don't plant more than you can maintain..because no matter what anyone tells you..beautiful gardens dont just happen, they are work...so be realistic about what you can devote to it. I personally think it is far better to have less, but to have magnificant spots, rather t han lots of weed filled beds...just my two cents....my first spot would be that area off the brick near the fence...a very doable size to bite off. And could have a great deal of impact. Don't forget hosta...they can add impact fast if you spend $ and buy large plants...and they do not need to be a forever plant..you can move them about as things change and evolve...

The biggest thing is the wall thickness - the thicker the better. If you live in a cold area, you could also ask about low temperature impact resistance. Digger Specialties (DSI) is good fence too.

In fact, Vinyl Fencing should NOT be sold as a DIY product. Here's why: I know everyone who had been in Construction or Reno for years believe it will be easy to install and they "Can do it", but this is very far from the truth. I had seen this 1st hand tooany times. Remember, Suppliers are simply selling to make profit. They do not care what happens in 10 to 20 years, nor if your PVC / Vinyl fence was correctly installed... They supply crappy and inaccurate installation instructions, making Clients to believe it is easy. Yes, it is easy if you know what to actually do. It is even easier installing it wrong.... Installed incorrectly, or as per supplied instruction, or as per YouTube Videos, will most certainly result in sagging rails, failing posts etc. We are Value Fencing PVC Franchise Group do it right: 1: We use Aluminium H- beams inside our rails. 2: Our panels span MAX 6 foot post to post, opposed to 10 foot. (10 foot is way too wide and will sag over time) 3: Post should be planted deep. We plant 33% of the post deep. (6ft fence post to be planted Min 3ft deep.) 4: Holes and Posts are to be filled with 25MPA concrete mix around 2/3 up. 5; 4x Y8 Steel ribbed re-enforcing rods should be I settled into all posts prior to filling with concrete. 6: Rail connectors are to be used, instead of cutting holes in posts for rails to slot in. (Cutting holes will reduce the posts strength significantly) Of installed this way, and your Vinyl fence material is of High quality, it will go 20 to 30 years minimum with absolutely no issues. Due to our proper installation method, we Guarantee our work for 20 Years. DIY and or inferior quality materials usually act up withing a few years with no o reliable to fix the mess. I strongly suggest to find a local expert in the field, using good quality grade PVC / Vinyl fence materials to assist in the installation. This way you have peace of mind knowing material quality and workmanship will stand the test of time. Here in SA, we have a saying: "Paying less always turn out expensive" We proud ourselves in our : "Everything in business is negotiable, except Quality"

We have a similar situation; a medium sized suburban yard with a mish mash of chain link fence. Replacing it with a privacy fence would be very difficult because a long stretch of it goes right through the middle of 40+ year old thicket of honeysuckle bushes with massive trunks and roots. They are great for privacy in the summer, but do almost nothing all winter. Neighbor has three motion lights that shine right in our windows much of the year! On one section with no honeysuckles we got the rolls of 6' reed fencing and tied it the 4' chain link with wires. It held up well for a few years but the wind and animals trying to climb it damaged it a lot. The wire holding it together is thin and starts to rust and break after a few years too. Cutting it back to 4' when it got ratty helped tidy it up a bit, but obviously a lot less privacy. It is a very temporary solution at best. Since your fence is not even on the property line, I concur that getting a new and more private fence pushed back to the line is a better solution. If that doesn't pan out though... the reed fencing is an option. Ideally you would pair the reed fencing with some type of evergreen shrubbery which will help as well. They help with noise too. We have a massive silver maple and previously had several in our yard and next door. Yews would grow under them, slowly at least. Sweet woodruff is a good groundcover for dry shade too, although it is not evergreen. If you do put in any shrubs, plant them far enough away from the fence so they have room to grow. I have seen our one neighbor out with a scissors cutting off just the very tips of our red-twig dogwoods that stick through the fence. People are strange.