Leak repair is obviously critical, and has to be done immediately.

Insulation will reduce your heating and cooling costs, but don't forget that attic insulation is by far the most critical, because the majority of your heat loss is upward.

Caulking is cheap and good.

Unless your windows are badly degraded, those should be a lower priority.

An energy audit from your utility will help you set priorities in the energy-bills arena.

Painting inside and out, and like-for-like replacement of worn carpeting and flooring, are also good ideas. Keep the house looking like civilized people live there :)

However, I'd suggest staying away from major updating, renovation, and upgrades. No kitchen or bathroom updates, no finishing the attic or cellar, and definitely no tearing down walls. Those alterations won't return their cost in improved house value when you sell.

As I see it, major renovations with your house torn apart are disruptive to your life and sometimes to your relationships. If you end up with contractor problems, slipping deadlines, or poorly done work, the headaches multiply fast.

It might be worth all that hassle when you have many years of enjoying the updates ahead of you, but since you can see selling and downsizing on the horizon, I'd definitely think twice. Maybe thrice.

That way, when you finally move and downsize, some growing family can move in, and make their own mark on your house.

You can hire an independent inspector to look for problems from your attic to your basement. An inspector doesn't have x-ray vision, but he will report any problems found. If you think you might have water infiltration you should work on that first as leaks can lead to structural damage. Roof leaks most often occur around a chimney, vent pipes, or along flashing (roof valley or attic dormer). How old is your roofing material? Asphalt shingles last around 20 years, so a home built in the 60s could be in need of its third roofing. Here is a listing of the average life expectancy for most Materials & Equipment.

If your home still has the original furnace or HVAC you might consider getting a newer unit. New units have much greater efficiency. Adding insulation to the walls and ceiling will do much to prevent heat loss. Replacing or upgrading things that lower your energy bills will also give you an improved household environment.

Start with roof. Replace as needed. Then work on insulation of attic. As stated, a good amount of heat and cooling losses are from attic/roof losses. Another approx. 30% are from windows and leaks around windows and doors. Depending on your location, this is critical upgrade. Next look at flooring. Most people looking today want wood floors or floors that look like wood. A mid-range engineered wood, with porcelain tile in wet areas would be good investment. Kitchen improvements gain the most in paybacks if done well. Without photos I can't really tell what you might be able to do. But keep that minimal or very careful if you tackle it. Paint is last. If you redo flooring, pick the flooring so the paint color works well with it, and then put flooring in after whole house painting. Upgrading lighting can have a great impact and by being careful you can do this relatively inexpensively. Good luck. If you post kitchen photos, I can be of more help.

Thank you for the advice. We actually have done the roof twice since we have been here. The last time quite recently. The dampness is in the crawl space along one outer wall. I’m concerned the same may exist in the finished basement area behind the walls. I’m also quite sure that there is little to no insulation behind the barn board walls in the basement. We did renovate the kitchen about 15 yrs ago and recently updated the look. I will be posting pictures when we get to that point as the cabinets are in good shape but are honey pine. I would like to explore the thought of either re-staining or painting.

We also replaced the furnace a few years ago as the furnace was the original to the house.

Rather than getting a basement specialist then insulation, etc. I’m hoping to get an “inspector” as noted above that would go through all the structural, plumbing, electrical, insulation etc and tell us what needs to be done.

would this be a home inspector similar to the inspector one gets when buying a new home or would a general contractor do this?

i appreciate the advice

You are on right track. I might look for specialist in areas of concern. House inspectors for sale time are more generalists
In either case, get referrals and talk to those people. Ask those people for others who used the resource. This secondary check up can reveal much more.