Here's the situation, I'm married, wife's a stay at home mom, have 2 boys ages 7 and 4 with a girl on the way in 2 months. We currently have a 3 bedroom house (1850 sq ft) we've been in for 10 years. Paid $110,000. It was really a mess when we bought it, not well taken care of but only 9 years old. Originally had a 30 year mortgage, but made bi-weekly payments. Refinanced ~6 years ago at 5.375% for a 15 year loan, 9.5 years left on this mortgage. Current Market value is ~$150,000, $65,000 is left to pay off (This is in Upstate NY). Never took a HEL/HELOC.
Done my share of work on the house, built a huge deck, built a shed, built a swingset, landscaped the front and back, finished the basement (kids play area/TV couch and computer area), totally gutted and redone a bathroom, new carpets in living room, bedrooms etc.
With the new baby coming, we're moving the 2 boys in together. The 2 kids bedrooms are kinda small, but we'll make due. I'm a little worried about when they get older 16/13.
Anyway, The kitchen is getting worn, would like to redo the whole thing (dishwasher is currently not built in) floors in kitchen, hallway and foyer are linolium and are looking bad. Front of the house is cedar sided, with vinyl on the sides and back, wife would like to replace all of this and just get it sided. Roof will need replacing soon.
So basically I'd like to redo the kitchen, new floors, re-side the house and put a new roof on in about 5 years. This is likely to cost $50,000-$60,000.
My current income is $70,000.
I have no debt besides the mortgage, I own my car free and clear (2001 Malibu) and currently leasing a Trailblazer for $280 a month (lease expires in August).
I have $150,000 in my 401K and ~$25,000 in an IRA. ~10,000 in saving currently.
The question I have is whether I should have this work done on the kitchen, roof, siding and take out a HEL to pay or should I consider selling this house and buying a new house for $200,000 that is relatively newer or brand new that has 4 bedrooms and won't likely need any work for a while.
I'm feeling like the $50-$60,000 I spend on the upgrades is a waste of money (I know it's not) and I'm not likely to increase the value of my home too much with these upgrades. Homes in my neighborhood probably average $150,000, while some are 165/170. I'm really having a tough time deciding if I should look for a new house in a few years, but I hate the idea of starting a new mortgage as mine will be paid off in about 9 years. I'm trying to hold off on the kitchen upgrade /siding as long as I can because I'd rather save up the money and pay it than take out a loan, I just don't think it's possible.
Thanks for any advice.
Also, I'm going to need a new vehicle in August and I currently carry the GM card with $3,000 in earnings, so I was leaning towards a lease again, maybe a minivan or SUV but I'd like to have room for 3 kids and stuff. Having $3,000 off is really making me choose a GM here. Any recommendations here would be helpful too.

