I don't think your budget is realistic at all if that is for the entire project (especially since there is baseboard heat, exterior BEARING wall etc. Yes the first thing to do is hire an engineer to determine if what you want to accomplish can be done.

Krycek- I'm no expert, but I've seen this done enough times on HGTV to know that if it's load bearing, you can't just cut a hole in the wall. You have to put up a temporary wall, open up the area of the wall you want open, and then frame it in with a beam and supports...then take out the temporary wall. You'll need someone (like a structural engineer) to determine if it's a load bearing wall and how much weight you need to support. This will determine the size and type of beam you'll need...and if you need any reinforcements in the basement or cellar to support the new beam.

I'm sure this is going to cost more than $500, but I would check with a professional before making any definite decisions. If it wasn't an external wall (nor a load bearing wall) then it would be MUCH easier to open up the space. Better to know for sure...than to guess.

Your budget is about what it would cost for a consult from the structural engineer that you need to create a report for the city to get your permit. Then there is the permit cost and the contractor cost. If the wall has electrical or HVAC in it, besides being load bearing, then your cost also just went up.

On a good day, with there being no hidden structural issues, what you want might cost you 2K if you DIYed it all. For a contractor to do the same job, you might be looking at 3K and up. More if the electrical and HVAC prove to be problematic. Plus permit costs.

And now onto the door project. That obviously needs the HVAC for the room to be re-engineered. How complex that may be will depend on the type of baseboard heating that you have as well as the insulation and window type and a whole host of other issues. You need to have a HVAC person come in and take a look at the system as a whole because if the current system is at the end of it's normal lifespan, just doing one change to it could take it over the edge, or, it could be an extremely cost foolish decision to not address the whole home.

Then, after the HVAC is addressed, you have all of the structural and cosmetic issues to deal with that you would have with any cutting a hole in the exterior envelope to your house. You want to be sure that it's done in a way as to keep your house weathertight as well as done in an aesthetically pleasing manner for the exterior and interior patches to the wall components. This is probably more than a 5K project and could cost as much as 20K if the whole home's HVAC and insulation will need to be addressed.

Krycek- The first thing I would do is get three contractors out to see your house and give you some free estimates. Tell them what you'd like to do (long term) and what you hope to do right away. That might give you some idea what some of these things would cost, what is necessary for permits in your area and whether you can change/move the baseboard heating.

If contractors are as slow in your area as they are in mine...you should be able to find some good people. What might normally be too small to bother with, might be a good 'quick job' between major projects. It doesn't hurt to call and ask. And remember, you want FREE estimates :)

Thanks for the guidance and opinions, everyone. I appreciate it.

There is no HVAC...just H. LOL. No ventilation, no AC. In any event, my budget was unrealistic so thanks for the heads-up.

We would not spend 20k on it...that's a bit overboard. I suppose if we want to move back we will just concentrate on doing something with the wall between the kitchen and the dining/living area. We could temporarily live with the situation as is.

I miss the land, but I do not miss the old jumbled up house. It's a shame because the main living area is set up like a modern house - living room, dining, and kitchen in a line.

Krycek- Houses can be fixed (over time) but land is....well, land! And for us, the views are like nothing we'd see in town :)