DH is planning to help his father pay his mortgage each month. We are a one income family. He is selling company stock in order to pay off his car. He will send his father the equivalent of this payment monthly. I am a small business owner that will eventually earn more when my youngest is in Kindergarten...but perhaps not enough to truly be second homeowners.
FIL is 75 years old. He has a modest SSI income which covers his mortgage but not his living expenses. He basically lives off a home equity credit line that he took out to help him remodel the home. The home has no staircase- but he did put in a wine cellar

One has to walk outside to access the lower level of the home. He also has a finished loft in the home but it can only be accessed by a 15ft ladder. The house needs about 100K of work min to be complete. I don't anticipate it will get done in his lifetime.
DH has an intention to pay the portion of the mortgage to increase the percentage of the home that he will inherit. His brother, who is penniless actually could use the home- but my husband does not want him to have it as he put many years into helping his father build the house and his brother has done nothing. FIL wants the home to remain in our family as a second vacation home. I do not really enjoy vacationing there, but could suck it up one week a year. It's a 10 hour trip to get there.
However, what is to be done with it the rest of the year? It needs major remodeling to become a vacation rental property. The cost of maintaining it will be at a minimum $1000 per month with the current mortgage. It is a prime location for tourists and could be appealing f we had money to put into it.
I truly think my FIL ouught to sell it, take his earnings and enjoy his retirement. He leaving us an albatross that my husband will likely never sell.
Our primary residence is in need of major remodeling as well. Our home is essentially a tear down. We are surrounded by McMansions and I would very much like to update it. It's 50 years old and still retains its original mid-century "charm".
Anyone have a similar scenario? Any advice is appreciated.