Painting front door

When the tenants moved out of one of our IP's recently, they broke one of the hideous pretend stained glass rose glass panels in the door and boarded it up.
We were quoted $3k+ to replace the lot.

So in a effort to make the house look less like a drug-house, while at the same time keeping the budget in check I've decided to have a shot at renovating it. Problem is that it's not in the best condition - we live near the ocean and it's pretty weathered, with some flaking paint and swelling of the timber at the bottom of the door.

NOt even sure if it's worth trying to fix but I figure it will be good practice for other painting projects. Anyways, I need a few tips please!

1 - How sanded does the door need to be before painting it? Just roughed up a bit?
2 - is it hard to make it look good- as in not streaky and uneven - considering it has mouldings etc?
3 - IS there a clever trick to cleaning up after using oil based paint?

Thank you!
Doors Plus often have front doors on sale with the glass panels you have described and for a lot less than $3k. Check out their website. Personally I wouldn't bother repairing and painting :)
We just repainted our front door after 15 years of weathering. We're not near the coast, but the rain had made the bottom swell and some of the veneer was coming up around the bottom 3 inches or so.

We took the door off the hinges and glued up the bottom. We got some cheap clamps from Bunnings and a piece of pine about 7.5cm wide and 100cm long. You can use this to clamp the veneer down. First you soak the bottom in glue and push as much as you can into the gaps as deep as you can go then clamp the lot with the wood. I think we put newspaper in between so the wood didn't stick together. Leave that to dry overnight. One tip - make sure the wood you use to clamp is a little shorter than the width of the door (we found this out the hard way - your door won't shut over night otherwise, and you'll have to use a chisel or something to make it fit! :)

You need to sand a fair bit. We used 120 grit paper to get off the old paint. You don't need to get all of it off, just the bits that are flaky. The rest you can sand with a lighter grit.

Remember to tape up the fittings, hinges and any glass with masking tape.

We used Dulux Weathershield. Looks pretty good afterwards. I didn't have any issues with streaky-ness. Work fast, paint from unpainted to painted areas, and put on a couple of coats.

Hope this helps :)
Normally add a piece of thin stainless steel strip , maybe 10-15ccm high at the
bottom of my doors if they get weathered and damaged , hides all the damage
and the rest of door looks good with fresh coat of paint.
Oil based paint is a pain the butt.

Go for water based high gloss outdoor for a front door.

Your pic of the door didn't come up, maybe try attaching it to the post.
I'd probably just replace it with a nice but economical door. It'll be faster (you are between tenants I'm guessing) thus reducing holding costs and hopefully enabling you to get a new tenant in quicker.
Yeah, doors aren't that expensive from Bunnings, would probably be easier to buy one and paint rather than mess around sanding and hoping for the best
We recently replaced a swollen and damaged front door. All up including buying the paint and a new deadlock came to about $330 DIY. Be careful, many of the doors are not solid. We did two coats of primer and three coats of coloured paint on the front and the edges, less on the inside. There is something you buy to add to the enamel to make it easier to work. The staff at the paint shop will know what it is called. We added a weather strip at the bottom. Have fun, it is very fiddly fitting the door.
We did consider replacing the door, but them we're stuck with the beautiful rose side lights - doors are cheap but sidelights aren't!

We're actually living in the IP for the foreseeable future, so want to have something a little but unrental like for the door.

Here's the door - take 2 on the picture

And this is what we're going for, but with more normal glass -

The timber at the bottom of the sidelight is swollen - have no idea how to fix that, if it's even possible? Can you take them out? I'm such a complete newbie with hands on renos, we normally pay people to do the dirty work...will probably regret it but I'm determined to have a go :)
Doors plus had similar door for around the 300 mark. Don't know if they are in Pert. I noticed the rose door as it is similar to my old house front door, whilst shopping for new front door for my new house