Siding/Windows Debacle

This is a great little concept.  There are so many articles lately about being content with what you have.  It's the key to happiness.  In a world where keeping up with the Jones' pretty much trumps everything, it's a daily struggle to take a deep breath and appreciate what we have versus what we want. It's all about one's outlook and perspective.

Case in point: the siding and windows debate going on in my house.  We own a 1950s Cape Cod style home.  It's always been painted and the windows we do have are sort of a hodgepodge collection of whatever the prior two owners installed, most likely based on availability and price.  We all have a budget so I can totally understand this.  This coming fall we'll have been in the home for six years so the house definitely needs to be stripped and painted or sided.  One of the two.  Painting is a huge effort for two people who work full-time and have a toddler at home.  Plus it'll need to be redone again and again every six to eight years.  So we enter the realm of obtaining quotes for siding and windows since pressure washing is much preferred over painting.  Well, the quotes come back at roughly 1/3 of what we paid for our house! That's way out of our current budget.  So we're back at square one and now just searching for professional painters to come quote the job. My husband and I have entirely different perspectives on this scenario.

I'm able to take a deep breath and say "Whatever, so we paint it.  It's the cheaper of the two options and buys us some time before we have to revisit this topic again."  Done deal.  Stop dwelling on it.  Move on.  My husband on the other hand takes this news as a slippery slope doomsday prognosis and believes the sky is falling.  "We're never going to be able to afford to put siding and windows on this house, it's a money pit, we need to get out while we still can!"  He begins researching newer houses with cheaper finishes and larger mortgages and harps on it day in and day out.  Now, there's nothing wrong with our house besides a few cosmetic updates.  The kitchen has older cabinetry and wallpaper and the one downstairs bathroom could use a remodel, but everything is solid (solid wood floors, solid structure, solid wood cabinets, etc).  Plus, everything is clean.  We have great square footage and a beautiful piece of property.  Long story short, he's giving me a massive headache everyday and his mood and our marriage is suffering from it. 

We took a drive this weekend to help Jayson take a much needed nap and it was so easy for me to see how good we actually have it when you see what other people's housing actually looks like in comparison to ours, even with the siding peeling.  People make do with much less!  I thought for a moment my husband got it, started talking some sense, seemed like we were on the same page.  However, this morning he's back to the doomsday speech.  I'm going to pull my hair out!!!

Anyone know any good local painters in the Schoharie County region or a good marriage counselor? We need to get past this debacle and get back to happier times where he can better appreciate what we have or all kidding aside the latter of the two is going to be our next option.