How can I fix up the outside of my house?

Sorry to hear about your Dad. I know, it's tough. Start with calling a reputable roofer and let him tell you what needs to be done. If you think you can do it yourself, go for it. I always give everything a shot, and if I mess up, then I call someone. You'd be surprised what you can do yourself, and you can get a lot of advice and videos on line as well. Good luck to you.

I would pressure wash the entire exterior and then you can assess any damage that might be there. If it needs to be painted or stained or some of it needs to be replaced etc. With the siding fixed I'd move on to gutters. They're not cheap by any means but a seamless gutter company will come in and do a great job for you.

Check with your local Habitat for Humanity. They may be able help or to connect you to a local organization or group that helps people.

Katy, sounds to me like you need a Live-in Handyman, you can trust, [Wink Wink, Nod Nod]. That is what your Dad Wanted, I'm Sure.

You need to check the wood for Rot. If there is no rot, [Blackening of Soft Spots in the Wood] then all you need to do is fill any cracks or Splits on the Wood with Silicon Paste on Sandpaper, or a 3×5 Index Card, [Or old Playing Card] Rub it on, and then Paint it with a Good Exterior Paint, [Kilz or Rust-O-Leum]

Otherwise you need to Scrape and cut out the Rotten wood with a Chisel and Hammer, Gently Tapping, or Drill it out, hen sand in the Hole by placing Sandpaper around the Drill Bit with masking Tape, fill it with Putty and Paint.

When Painting, Keep in Mind the General Purpose of Paint:

Paint is to Restore and Protect.

Paint does little more than that.

Paint is not Putty, Spackle, Linoleum, Minwax, Mister Clean, Ivory Soap, Formby's Wood Treatment, Solder, nor Glue, although: Many people Do tend to think paint is a Fine Substitute for these, and more especially: Substituting Paint for Ivory Soap, Mr. Clean and a Good Sized Rag.

[On that Topic, I am sure your dad has a Bag of Old T Shirts, Somewhere, probably under the stairs to the basement, in a White Bag, whatever you do, do not discard these, these are great for use as Cleansing Cloths and Rags, but also for wrapping around a Paint Roller [3/8th Nap Roller] for small paint jobs around the house, so you do not need to as vigorously clean the roller].

You may want to check out the following family handyman website regularly for tips:

https://www.familyhandyman.com

I do, and subscribe to their newsletter, moreso lately I really enjoyed:

https://www.familyhandyman.com/woodworking/40-outdoor-woodworking-projects-for-beginners/view-all/

Keep in mind we are always here at Hometalk to help.

Good Luck with your Projects!

And Congratulations on acheiving your Status as a Homeowner!

Let the Dreams and Maintenance Begin...

if you want to sell it and not have any work, sell it as is for a low price. lots of investors out there looking for rehabs.