Money Matters
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updated in comments: new computer(s), WWMMD?
H and I both want new laptops. Mine is slightly older so we decided that I would get one this year and he would get one next year. I put mine in the budget this year and we should have no issues paying for it. Our budget is flexible at this point and we know we will have a bucket of money available for some bigger purchases (hockey tickets, landscaping, vacations, computer, etc.). How we use that bucket can change according to our discretion and we can easily use it for a second computer. If we don't use all of the bucket then we will increase savings with the leftover. We have a separate investment strategy from this budget and investing the leftover money is not something that factors into this budget equation. So any leftover money going to savings is not going to earn any kind of attractive return.
I'm still exploring options for what I want to get, but overall I don't care much as long as it meets my basic needs and $1,000 should cover it. We looked at a Lenovo that fell into this range.
H is an IT guy and is insistent getting a Mac. His will probably be closer to $2,000. Macs do not go on sale (right?).
I asked the best buy sales guy if he would give us a deal for buying 2 computers and one of those being a Mac. He said yes and that he could probably get us $100 off of each for a $200 savings.
So now we are thinking about getting both computers this year since we can save a little with a bundled purchase. WWMMD?
ETA: In case anyone is wondering, my laptop is 11 and H's is 9 years old.
Re: updated in comments: new computer(s), WWMMD?
All that said if you have the cash I might take advantage of the deal you'd get by buying two at the same time. Both of your laptops have held up for a long time and I don't think it's unreasonable to replace a 9 year old laptop a year earlier than originally planned.
I think I can probably get something lower than $1,000 for myself since I really don't care. The $1,000 includes buying Office and is the max I will pay--I'm going to do some more research before deciding what exactly to get. I don't need to buy more computer than I need but I also don't mind spending a little more for something nice since I will keep it for a long time.
I think H's will be up to $2,000...maybe a little less. But that includes everything: extra memory, apple care, etc. H is an IT nerd and I'm ok with him spending more in this area since it is important to him and since the computer will last a long time.
TTC since 1/13 DX:PCOS 5/13 (long, anovulatory cycles)

Clomid 50mg 9/13 = BFP! EDD 6/7/14 M/C 5w6d Found 11/4/13
1/14 PCOS / Gluten Free Diet to hopefully regulate my system.
Chemical Pregnancy 03/14
Surprise BFP 6/14, Beta #1: 126 Beta #2: 340 Stick baby, stick! EDD 2/17/15
Riley Elaine born 2/16/15
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www.5yearstonever.blogspot.com
It really depends on what you need it for though.
And no, macs really don't go on sale.
TTC since 1/13 DX:PCOS 5/13 (long, anovulatory cycles)

Clomid 50mg 9/13 = BFP! EDD 6/7/14 M/C 5w6d Found 11/4/13
1/14 PCOS / Gluten Free Diet to hopefully regulate my system.
Chemical Pregnancy 03/14
Surprise BFP 6/14, Beta #1: 126 Beta #2: 340 Stick baby, stick! EDD 2/17/15
Riley Elaine born 2/16/15
TTC 2.0 6/15
Chemical Pregnancy 9/15
Chemical Pregnancy 6/16
BFP 9/16 EDD 6/3/17
Beta #1: 145 Beta #2: 376 Beta #3: 2,225 Beta #4: 4,548
www.5yearstonever.blogspot.com
And as others have said, Mac pretty much never goes on sale, but I don't see a problem spending money on them if that's what he really wants. Especially if he already has one and is probably invested in accessories and software already.
Buying a new Mac, not onsale, is a given. It is just a matter of if it is this year or next year. Buying it this year with the other computer offers the opportunity to potentially leverage it for savings that won't be available if the Mac is bought later by itself.
I usually don't recommend this @csuave, but do you really need Office? As in do you exchange files with other people? If not, you could look into some Office alternatives. I use one on my own laptop, but I'm not exchanging documents with others and I also have a work laptop with Office on it for the rare times in my life where it must absolutely be done in Office.
And like julieanne mentioned, you could load an older version of Office on the new laptop. Remove it from the old one and reload it on the new one if you have the install media.
The one thing I will mention. I have a laptop that dates from 2008 right now. I buy the biggest baddest machine I can get my hands on and keep it till the darn thing dies. In which case, feel free to spend more money on it as all the updates, etc will gradually slow the machine down. If either of you are techie, you can mitigate that somewhat by reinstalling now and then. However, if you're going to replace every couple of years to stay current and really don't do anything but surf the web and basic Office tasks, then I agree, you can get one of those $500 machines with no issue. I will note, don't get the cheapest thing you can get from the big box stores. They don't age well. They'll have the bare minimum specs for whatever they're loaded with and as you update software, patches, etc. the machine will no longer have enough umph.
I guess put me on the side of anti-paying $1000 for a personal computer for yourself unless you need some serious power behind it. I think there are lots of great options on the market for way less than that, and you can download Libre Office as a FREE alternative to paying Microsoft's ridiculous prices.
I don't use Google Docs, but I do use the LibreOffice (actually it's predecessor) that @labro mentioned above.
After looking at 3 different contenders I settled on a Dell with solid state. Regular price $600 but on sale for $550.
H decided he could scale back a little from the Mac he was originally looking at and found one with a sticker price of $1500. It went on sale for $1300!
We told the BB sales guy we were working with that when we originally went in there was talk of a potential extra discount for buying 2 computers. I wasn't expecting much since they were both on sale and the Dell was cheaper than the one I was originally looking at but he talked to the manager and got us an extra $75 off!
In addition to that $325 savings we bought gift cards for 5% cashback on the credit card and got fuel discounts with the gift cards. Those discounts are about an extra $130.
Since I was happy with where the prices came in we decided to flex the budget and do both computers this year. We've actually had a recent increase in funds available to our discretionary budget (my bonus and BnB income) so it was good timing to change the budget for this purchase.