Advice for siding, soffits, and facsia

Hey all I need help trying to figure out what to do with my 100 year old rental property. Specifically the siding, soffits, facsia, and because it's 100 years old it has no insulation. When I purchased the property it had already declined under differed maintenance, and after fixing up the interior now I'm on the exterior and I have no idea what to do. Here is my goals with the exterior project.

1.Fix all damaged areas and get a reasonable seal for a 100 year old house.
2.Improve the curb appeal for future residents.
3.Preserve as much of the historic look of this property as possible.
4.Keep costs way down because it's a rental and ROI is king.

That being said so far I've got 1 estimate for $15k for vinyl siding and 3/4 inch foam board, and that estimate didn't include soffits and fascia. I know the house is huge, but $15k to just slap vinyl over the current exterior seems ridiculous, and its really only goals 2 and 4 that it "kind of" accomplishes.

I can do the work myself. I've done just about everything except siding with reasonable results for a DIYer. So would you tear off the old siding, insulate in the walls and then vinyl over the top? Do it in small sections to keep it reasonable? Am I over thinking it and just let somebody slap siding over the top? I've attached some pictures.

Also... how should I insulate from the outside in? I assume it's a mold problem if I staple up paper backed insulation with the paper facing the outside?

The insulation should have been added from the inside not the outside for many reasons.
If the wall was opened up you could have updated wiring, filled any holes in the top and bottom plates with spray foam, had the vaper barrier facing the right direction.
How many prices did you get on doing the siding. If just that one get some more.
Anything vinyl has gone way up in price and is going to go up more since it's made from petrolium. Siding I was buying last year for under $50.00 a sq. is now $80.00.
If you now go with 3/4 foam (very expencive) all the window and door trim will need to be built out so the siding trim does not sit in recessed to the wall.

That was the 3rd estimate I got. the first one was for Sears metal siding and when the guy got out of his car at the house he was already laughing.... he basically asked me if it was over $30k would I be interested and I said no and he said ok then our product is not for you. The second one after meeting the guy it was unclear exactly what he wanted to do and how much it would cost. The most I got out of him was around $7.5k a side but he couldn't even really stick with that so I just told him thank you for his time.

When we did the inside we just patched and repaired the lath and plaster walls. So no additional insulation was added. The repairs inside were more about fixing the horrible repairs the previous owner did rather than fixing anything original to the house. Now that I've actually got the chance to put in insulation I would like to do it, but it doesn't sound like there is an advisable way to do it from the outside?

So Joe if it where you, you would pull off the old and start new? Obviously I can't match the old material without getting it custom made (It appears to be around 3 and 1/2 inches of exposed material and all I have found is 4 inches in vinyl).

It is possible to open up the wall from the outside and insulate, but keep in mind that the outside sheeting is what holds the house square. If you put foam on the outside, you are adding a vapour barrier to the outside and any water entering the wall will not be able to dry. With insulation you will have more water condensing on the windows, so they should be pulled and re-installed so water can be deverted out.

Nealtw would a layer of Tyveks (or however you spell it the "house wrap") make any difference for the vapor barrier?

As I understand it house, wrap products stop water but allow vapour thru, moisture getting in the wall has a chance to get out if it can evaporate, Vapour barrier is on the inside of the studs to prevent moisture from the house entering the wall cavity. Oil base paint on your old house plaster does have some value as a vapour barrier and nothing is 100%.
Your house didn't rot because there is lots of air everywhere, you want to really understand everything before you change how the house works. Others will be along with diff. opinions and then you will have to figure out what to do.
Foam and drywall on the inside is what I would consider.

What are the layers on the outside of the house now?
I think I saw where it now has aluminum siding on it. A house that old most likly orginaly had wooden siding and someone went over it with the aluminum.
If so all the old aluminum siding and the alumium trim needs to come off. Once that's done I'd go over the walls with fan fold foam and then vinyl siding not aluminum.
Aluminum siding is almost never used any more and the cost will be about double what vinyl siding would be.
Vinyl siding can be bought smooth, wood grain, double 3, 4 1/2, 5, or even 7".
It can also be beaded, flat, Dutch lap, profiles.
Any real siding company should be able to tell you exactly what it would cost with no problum.
I never ever would call Home Deopt, Lowes, Sears, ECT. for a quote on installing anything. The reason is the cost, they do not install anything, the independent contractors do the install and the other company gets a kick back.
I'd look under siding in the Yellow pages instead, or ask any General Contractor who they use.
If they suggest also having all the exposed wood wrapped with coil stock, go for it. Silly to have no maintaince siding and leave the wood still needing to be painted.

We did blown cellulose insulation on our 1 story bungalow. My grandma did the same on her 2-story old house. You have to put holes in your clapboards and sheathing to blow the insulation in, but if you are going over with vinyl siding no one will see. It has worked well for us.

We DIYd the vinyl siding with 1/4 inch fanfold on our bungalow. The door and window trim was done with PVC boards to replicate the look of the original trim and to bump out to the level of the new siding. I think there are now similar products on the market with a J-trim style cutout on the back to accept the siding, but we did our own cutouts. We used vinyl soffit and vinyl fascia/rake board trim to snap over our 1x6 trim by the roof. I am not sure how you would cover your arched window trim, but you might be able to find a reasonably priced product to do that too.

Just realize - vinyl siding has a life span similar to the shingles on your roof. Eventually it will get brittle and need to be replaced. I think higher quality (aka more expensive) siding has some UV inhibitors to slow down the process, but almost nothing lasts like well-maintained clapboards.