Money Matters
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Re: Budget thoughts needed
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
Another option we could look into is having insulation added behind the siding. When we investigated it a bit, they told us that we would have to replace our siding (we have aluminum that's 20 years old). The rough estimate for siding, insulation, and house wrap was $17-20k. We will likely eventually do that if we end up staying in the home. Our plans were to replace the siding and roof at the same time, and insulate from the outside in.
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
I would contribute less to retirement, because it seems to me like you should be including that $100K in your future retirement plans. If you aren't going to touch it and are going to invest it, it should be part of your future retirement calculations. I really don't think you need to contribute 17-19% to retirement AND have the $100K investment.
Addressing some of the smaller things:
I would get on balanced billing for the heating. It will make your bill higher some months but it won't hurt as much in the winter months. It all comes out to paying the same over the course of the year, but it is more evenly distributed and easier to budget.
I really can't see replacing a vehicle every 1 1/2 to 2 years, unless you are buying junk vehicles. In that case, invest in something that is going to last much longer. I live in a rural area. 30K miles a year is actually kind of normal around here, especially for people working in the energy industry. This should not mean you have to replace a vehicle after 2 years, especially since you are also spending a lot to maintain them.
$100/month on clothes does seem like a lot to me; I mean, it's a nice luxury if it can be afforded, but this is something that I think could easily be reduced if you are trying to move funds around to other priorities. I budget $100/month on clothes but I would cut that if it meant I had to give up our vacation budget.
$660/month for food ($500 groceries, $100 eating out, $60 beef) seems pretty high for 2 adults and a baby. It sounds like this is an area that you could easily trim.
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
It's funny, because I feel like the clothing budget is very lean and is hard to keep within. But we spend $300/year alone in new shoes for H (steel toed boots for work, basketball shoes, and every day shoes). Then I run half marathons, so there's another $250/year in running shoes for me.
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
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
The way we viewed it, if he drives this car for 2 years and we paid $7k for it. He will put 60k miles on it, and it will probably still be worth around $4k. So we will only need to add another 3-4k to that amount in order to replace his with something newer and with lesser miles.
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
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