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On the painting front (as I just finished painting all of my soffits today in preparation for new gutters), prep is more important than anything else if you want the paint to last. That means cleaning (I used a pressure washer first then wipe down with TSP solution, but use a bucket and brush for windows), then scraping anything loose up. This would be the time to attack rot repair if you need to, then sanding the edges of any paint that came up, finally wipe everything down with a damp (err to the dry side if you want to paint right away) and paint. Raw wood should really have a primer first, I tend to skip that for anything smaller than the size of a dollar bill though, unless I'm priming Other things at that point.
Use the best paint brush out there, IMHO that's a Purdy brand. If you clean it well, you'll have it for many, MANY years.
If you used a home inspector to verify the home before purchase, their report will tell you everything you really need to know about the house. Get cozy with that report and search for maintenance tips on each item (specifically the model you own, which should be listed) to see what you should be doing.
sometimes utility companies have specials on furnace check ups...it would be a good chance for a person to walk you thru how to work your furnace.
I also think you tube or HGTV would have some helpful do it yourself videos.
Location: New Albany, Indiana (Greater Louisville)
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If you have a crawl space you need to check the openings around the perimeter of the house. If you have nice covers you can open or close them with a screwdriver. In the winter you want them closed to keep the cold out, in the summer you want them open to prevent mold.
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