Consider yourselves warned - as the title suggests, this is not a fun thread.

Taking full advantage of last Saturday's beatiful weather, I decided to climb up on my roof and remove some of the moss that was growing. I have suspected for much of the last year that my roof might be on its last legs (there have been several smallish sags visible near the top since the end of last spring). Walking around up there confirmed my fears - this summer will be the time to replace it.

My first thoughts were about how I would come up with the money to replace the roof quickly enough to get it done this summer. Then, as I started checking out the rest of the house, I was reminded that my windows are failing (badly), and that I had been thinking about putting a hardwood floor in the living area, replacing the kitchen cabinets.... Long story short (at least by my standards), I ended up at the bank on Monday to find out what options I might have in the way of restructuring my mortgage. The good news is that I left with several reasonable options. The bad news is that none of these options stands out in my mind as the clear best decision. Here is where I start reaching out to any of you who are experienced in such matters for some friendly advice.

What I believe are my best options, and a few of the associated pros and cons, are as follows:

1. Refinance to a new 30-year mortgage, with cash back on closing to cover the repairs/improvements I want to make.
Pros: To do this for the amount of money I need would only increase my current mortgage payment by about $20/month, and because this would be a cash out situation, I would not be faced with any requirements to complete the work on an aggressive schedule.
Cons: Even considering the value added by the improvements, I would still stand to lose as much as $10K in equity, which would limit my ability to move, should I decide to do so, for at least a few years.

2. Refinance to a new 15-year mortgage, with cash back to cover the repairs/improvements.
Pros: I would need to pay only about $275/month more than my current payment to reduce the term of my existing mortgage by 7 years, the repairs would get done, and I would own the house in 15 years, having saved a ton in interest in the process.
Cons: My payment would go up by $275/month. In these uncertain times, that could mean the difference between keeping my house and losing it should anything unthinkable happen.

3. Refinance to a new 30-year mortgage with a TBD sum of cash tied up for home renovations and add on to my tiny home.
Pros: Much-needed space added to the house, happier wife and kids, work all done by contractors and within 6 months.
Cons: Significant (TBD) increase in mortgage payment, restrictions around renovation loans require work to be completed within 6 months (and strictly by licensed contractors, which eliminates cost savings opportunities associated with doing menial work myself), and I end up with the dreaded "nicest house on the block," which becomes a risk (or so the realtors say) when it comes time to sell.

4. Fix the roof, sell the joint, and move.
Pros: New, presumably larger home, in potentially favorable location. With interest rates low, this is a good time to buy.
Cons: Mortgage payment approximately double, ability to move dependent on sale of current home.

It seems to me that all these scenarios accomplish something good, but they also end up costing me money, in some shape or form, in the long run. Do any of you have any advice/experiences to share that might be helpful? And, more specifically, are there any bankers out there who can tell me which options tend to favor lending institutions more than the others?

Thanks as always.