Fitz......you're asking the right question. Where do I start? I would start with the Architect.....not to upset any of the excellent designers out there (myself included, not that I call myself excellent, I'm a designer / project manager / contractor) and develop a Master Plan to follow for the next few years.

Next I would look at what I could combine...... you say you want the roof done ASAP, well at the same time do the Fascia work and possible the porch update if it will involve your roof line........combine related projects if possible.

A good set of plans is a must........for pricing and scheduling....always keeping the Master plan in mind.

Plan and schedule logically and as priority dictates. Meaning, it makes no sense to do something like a Master Bath and Kitchen update and then put in a new HVAC system that requires you to start punching holes in your just finished projects. or, for that matter, windows and new doors.

If it was me I would look at something like this for a logical sequencing:

New roof , fascia and porch update.
Convert den back into garage.... (you'll need the materials storage space and work area if you're going to be doing any of this work yourself).
Back door egress, new windows and doors.
New HVAC system
Kitchen update.
Master bath update and possible hall bath update combined (depending on scope of work you have in mind).
New wall and ceiling finishes (am assuming new wall isn't part of one of the other projects and the ceilings is the remainder of your ceilings.....you would included ceilings with specific areas and projects).
New fence and any other exterior work (i.e landscaping, whole house painting, etc.,etc.)....

Just my opinion.

It depends on the area you live in, but having a different pro to do each area is perfectly fine. You can hire a designer to do the plans all at once- unless you are taking walls down or gutting rooms to the studs an architect is not required. If you are worried about load bearing walls etc then you would an architect or engineer. If you are going to take a while to do the projects and are not sure what you want, find a trusted designer that will be with you for the long haul. Let them get you through all the stages. But tackling the roof is easy- just hire a roofer that is qualified. You do not need anyone else. Not sure where to go- try Angie's List or if you see someone getting a roof done ask the neighbors for a good one. It is very important to get someone qualified and who guarantees their work. Don't let price be your only concern here. Roofing goes for about $150- 200 a square w/materials. (A square is 100 square feet) This does not include tearing off the old roof either- sometimes you can go over the existing roof if there are not too many layers. Code generally will not let you have more than 3 layers sometimes it is two. Get several bids, be smart. Exciting, have fun!

Kutch, thanks for the insight to sequencing. It's a perfect example what I don't know to think about! New HVAC could possibly/maybe mean new holes? Who knew? The pros, that's who!

KK, thanks as well. Since this may be my retirement home or even a rental down the line, I'm considering universal accessibility as changes are made. I don't know a load bearing wall from a wide load truck so your counsel is spot on.

Great advice from S. Thomas Kutch. I agree talk to an architect first who is able to come up with an overall master plan and the final look when the project is done. As for construction sequences, it's ideal to group all the projects and have them done all at once, such as updating all the bathrooms and kitchen first, then the bedrooms and main living area, and finish with the exterior.

Great advice above!

Always start with the end in mind. That is, have good plans!

The scope and nature of your project and/or your location may not lend itself to an architect (nor your budget, potentially), but have a pro (architect / designer / design-build firm / contractor) map out with you costs, sequences and plans.

You'll, at that point, have clarity as to how to continue to the next step.

Good luck!