Would love to expand more in VT (ski resort areas...still pricey), central/western MA, the Berkshires.

Im missing a few chapters of rental investments, the after math! 

But then again, when I lived in SC we paid 500 per sq, ( 55 SQ do the math, OUCH ) NO other choice they ALL ripped you off LOL  Furnace 80k BTU 700 bux material at HD.

I would certainly love to build a vacation home for free though if the math made sense.  

Do the math now, and if it makes sense under the current high rates than you will most likely be fine down the line. 

This doesn't mean ignore rental increases, but at the end of the day it is a math problem. 

U want your parents to talk to their CPA FIRST.. if they go the development route they are now ( depending on the amount of units) creating inventory.. which will be taxed at ordinary income rates ( very HIGH)if they just sell they can 1031  and move on to something else.. many times when you run the math consider the risks of a partnership.. the sale of the land is far better than thinking your going to make some profit.. 

So there are a few ways to look at this, the 1st question is are you sure your renovation’s will double the property value, most renovations on primary residences, your lucky to get 60-70% of the dollar cost back out upon sale, so really nail down your comps, than you have basically a math problem if your rate on your primary goes up how long if ever before that extra payment is more than 400k in taxes, that’s just a simple calculation to help you decide, but I suspect you actually have a different question here, from a purely financial perspective my guess is the best option is to do anything to avoid that tax hit, but one of the reasons to make money is to spend it on things that you enjoy, based on your overall financial picture and a subjective view of how much enjoyment you will get out of a renovated home, you should decide if you want to roll your profit into another deal or “cash-out” your winnings, I love cars and I’m willing to spend more than is fiscally smart on them because they bring me joy, there is nothing wrong with that, but i don’t think it’s a fiscally smart choice, without knowing your exact property id imagine a renovation would fall into that category, so that’s the terms I would use to decide.

In that case, the math doesn't support paying a couple thousand dollars in fixed fees to a title company. 

The basic math they used to describe "replacing" your income was a bit shocking.