And, if you're going to spend that much on a property, I would think it would be worth a pretty significant investment in getting to know the market.  

So you figure 25k for a down payment equates to a property worth about 166k that will need maybe 75k in repairs let's say for a total project cost of 241k (loan amount would be 216k approx), then holding and closing costs of about 15k.Now when the project is over and you sell, you'd want to try and sell it for 241k/.70 = 340kish. 

Its based off of what it will be worth after the renovation is complete 

I agree with Ken, get some costs and see if it's worth it but depending on how old the roofs are on your dwellings if you have a claim and replace the roof your rating might not really change. 

I would have to say that the curtain rod would be easier, but if you are worried about caulking and don't want to risk water damage then the glass doors might be worth the investment.

Because it's a family, my plan is to increase their rent each year until at market average.

And in the end, what is your time worth?

The short term kick in the stomach will be worth it

I have a 2bd 2 ba vacation rental worth of furniture supplies, living room, kitchen, laundry room everything you would need turn key for a airbnb or VRBO where is a good site to sell it all in one and not dirt cheap? 

On a 15-year note, other people are paying for your lovely retreat, and after the loan is paid off, it could be worth double or triple what you paid!