Money Matters
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This is a little long:
DH and I are trying to figure out how to plan the next 4 years or so with the girls. Currently, we live in a 4 bedroom (2 upstairs, 2 downstairs- we're all upstairs and the girls are sharing a large bedroom. The bottom 2 are an office and guest room/sewing space which we could technically let them use when they get older, but we don't feel comfortable having them downstairs when they're little), 2 full bath (1 up, 1 down) house. It's older- built in 1926, bungalow style, about 1600 sq ft. We've done a ton of work to it and it's in really good shape. Houses in our current neighborhood move quick- most are sold within the first week of being listed and I think ours would get multiple offers if we price it right.
DH's new district/job is 25 minutes away with about 15 minutes of that on the highway. I'm about 17 minutes from my work and it's all city streets. The girls' elementary school is great- rated really well, in a nice neighborhood. Their middle school and high school are fine, but don't even make the top 20 in our area, but either is the middle/high school I went to and I did just fine.
I started looking online at some homes in 2 districts (one very close to my work- #7 in the area and the other in DH's district - #2 in the area). Houses are 2500-3000 sq ft and at least $300K but would need significant updates. Most are all carpeted (some without hardwood floors underneath), kitchens/baths need gutting, etc. The homes close to my work are part of an older neighborhood (homes built in the 1920-30's) so who knows what we could be getting into (basement problems, sewer lines, roof, electrical, etc)
Right now, we owe $97,000 on our mortgage and it will be paid off in 2025 (we refinanced in 2010 to a 15 year mortgage at 4%) if we stay here. Based on all of the renovations that seem to be consistent with the houses in the other school districts, is it a good idea to pay off this house fast, have no mortgage, buy a new house, and live in the old one while we work on the new house? I figured if we add $1500/month to the principal (which would mean DH and I would not be getting new cars until DD#2 is out of day care- mine is 2003, DH's is 2006), we can knock it out by February 2019. DD#1 would be in 4th grade, DD#2 would be in 2nd grade and DD#1 would be leaving her elementary school that June (only goes up to 4th grade due to consolidation/redistricting for the 2016-2017 school year). If we buy a house in spring 2019, DH can work on it the bulk of the summer (he's a teacher) and put our house up for sale when we're closer to being able to move into the other house. We have significant savings plus a $30K CD that just sits there and could be used for a DP (10% or so) initially for the new house. Once we get the $ from our current house (I'm thinking $200K), we could add more to the principal, refinance, lump sum to drop PMI, whatever.
Any thoughts? Other ideas? Trying to figure out some options without disrupting the girls' lives too much and leaving us house poor.

Re: MM Hypothetical Dilemma
At that point in time, it sounds like your current house would be fine for your family. The two oldest girls would be 7ish/9ish, which seems old enough to me to have bedrooms on a different floor from you all. Or the middle one could still stay with her younger sister in the other upstairs bedroom, if 7 still feels too young for you.
But now I'll go to your hypothetical situation. Your current plan sounds good, though I'd be a little concerned about the older cars. What if one (or both) of them breakdown and the repair is more than the car is worth? You all might end up having to replace a car and/or face large repair bills.
Also, you are looking at the housing prices, availability, demand as to what it is at this point in time. It could be a very different picture 3-4 years from now. Not necessarily worse, but different.
I'm not making any recommendations one way or the other, but here are some other options to mull over:
--You could buy another house sooner before you sell your current house (with the mortgage still on it). Fix up the new house, move in, and sell your current house. Of course, the bad side is you would need to carry two mortgage payments for 2-3 months and your debt to income would need to be in good enough shape for a bank to allow that. Ooohhh...just thought of another downer. The bank might require a 20% down payment for a second home loan.
--This would require a bit more disruption than you might want, but you could find a house to buy. Buy it with a contingency of selling yours. Sell yours. Than either live in the house while it is being fixed up or move into a month-to-month rental house . You could get a construction loan included with the house purchase and that might allow you to fix up the new house in a fast time frame.
With your current plan, you might have to wait 6-12 months after the purchase to refinance and drop PMI, even if you do pay a lot of the principal down. I'm not totally sure about that for an owner occupied home purchase, but non-owner occupied home purchases definitely need 6-12 months of "seasoning" before they can be refinanced. Plus, refinancing does come with fees and costs.
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
As a general rule though, I am absolutely not in favor of paying off a house early that you don't intend to stay living in. I'd much rather save that extra money every month and then it's yours at your disposal when the time comes to move or do renovations, whatever. Your mortgage is so low, unless you were worried about not covering the payoff when you sell, which it sounds like you aren't, I wouldn't bother paying it early. But I much prefer having my money to use as I choose when the time comes rather than tying it up into pre-paying a mortgage.
If you cannot live in your house as your kids age and you want to relocate, I would consider starting to look now and if you find a house you like use the contingency for selling your home. Like others have mentioned the market can change, and I've heard that interest rates on mortgages are expected to start increasing in the next few years. I would start putting the extra $1500 towards a down payment versus putting towards your current mortgage.
If it were me I would want to start looking before the size of my home became a problem for my family. Another thing to consider is whether or not your kids will be in the same school district, it can be difficult on kids to move schools, so you may want to consider that in your timeline. I know you mentioned above that DD 1 will be going to middle school at the same time as moving if you go with your current plan that is a big change for any kid (new school) and on top of that she might not be with any of her friends. Good luck on your decision!
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
Doh! I hope I my above post didn't jinx you on the car! Sorry to hear about that, but at least it is a shorter loan than the typical 60 month and the interest rate is low.
Sounds like a good plan for getting into a bigger house sooner, but without putting on too much financial strain.